Compound for organic electric element, organic electric element using the same, and electronic device therefor

ABSTRACT

Provided are an organic electric element having a first electrode, a second electrode, and at least an organic material layer formed between the first electrode and the second electrode, the organic material layer comprising an emitting layer and the emitting layer comprising a mixture of host materials which improves luminous efficiency, stability, and lifespan of the element; and an organic electronic device comprising the element.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of U.S. patent application Ser. No. 17/043,595, filed Sep. 29, 2020, which is a national stage application, filed under 35 U.S.C. § 371, of International Patent Application No. PCT/KR/2019/003116, filed Mar. 18, 2019, which claims the benefit of Korean Patent Application No. KR 10-2018-0036886, filed Mar. 29, 2018, and of Korean Patent Application No. KR 10-2019-0029346, filed Mar. 14, 2019, each of which is incorporated by reference herein in its entirety.

BACKGROUND Technical Field

The present invention relates to compound for organic electric element, organic electric element using the same, and an electronic device thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenon that converts electric energy into light energy by using an organic material. An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed there between. Here, in order to increase the efficiency and stability of the organic electric element, the organic material layer is often composed of a multi-layered structure composed of different materials, and for example, may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like depending on its function.

Bis-type cyclic compounds including heteroatoms have a very large difference in properties depending on the material structure, and are therefore applied to various layers as materials for organic electric elements. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties are different depending on the number of rings and the fused position, and the type and arrangement of heteroatoms, therefore application development for layers of various organic electric elements using the same has been progressed.

In a phosphorescent organic electric element using a phosphorescent dopant material, the LUMO and HOMO levels of the host material have a great influence on the efficiency and life span of the organic electric element, and depending on whether electron and hole injection in the emission layer can be efficiently controlled, charge balance in the emission layer, dopant quenching, and reduction in efficiency and lifespan due to light emission at the hole transport layer interface can be prevented.

For fluorescent and phosphorescent host materials, recently we have been studying the increase of efficiency and life span of organic electric elements using TADF (thermal activated delayed fluorescent), exciplex, etc., particularly, and many studies have been carried out to identify the energy transfer method from the host material to the dopant material.

Although there are various methods for identifying the energy transfer in the emitting layer for TADF (thermally activated delayed fluorescent) and exciplex, it can be easily confirmed by the PL lifetime (TRTP) measurement method.

The TRTP (Time Resolved Transient PL) measurement method is a method of observing a decay time after irradiating a pulsed light source onto a host thin film, and is a measurement method that can identify the energy transfer method by observing energy transfer and emission delay time. The TRTP measurement is a measurement method capable of distinguishing fluorescence and phosphorescence, and an energy transfer method in a mixed host material, an exciplex energy transfer method, and a TADF energy transfer method.

As such, there are various factors that affect the efficiency and lifespan depending on how energy is transferred from the host material to the dopant material.

Since the energy transfer method is different depending on the material, the development of a stable and efficient host material for an organic electric element has not been sufficiently performed. Therefore, development of new materials is continuously required, and especially development of a host material for an emitting layer is urgently required.

Reference KR 101170666 B1 was used as a prior art document.

DETAILED DESCRIPTION OF THE INVENTION Summary

The present invention has been proposed in order to solve the problems of the phosphorescent host material, and an object of the present invention is, by controlling the HOMO level of a host material of a phosphorescent emitting organic electric element including a phosphorescent dopant, to provide a compound capable of controlling charge balance and of improving efficiency and lifespan in an emitting layer, and an organic electric element using the same and an electronic device thereof.

Technical Solution

In order to control the efficient hole injection in the emitting layer of the phosphorescent emitting organic electric element, by containing a second host material in combination with a first host material as a main component, the energy barrier between the emitting layer and the adjacent layer can be reduced, and the charge balance in the emitting layer is maximized to provide high efficiency and high lifespan of the organic electric element.

The present invention provides an organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, wherein the emitting layer is a phosphorescent emitting layer and comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 2:

The present invention also provides organic electric elements and electronic devices using the compounds represented by the Formulas.

Effects of the Invention

By using the mixture according to the present invention as a phosphorescent host material, it is possible to achieve a high luminous efficiency and a low driving voltage of an organic electric element, and the life span of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE is an illustration of an organic electroluminescent device according to the present invention.

100: organic electric element, 110: substrate 120: the first electrode(anode), 130: the hole injection layer 140: the hole transport layer, 141: a buffer layer 150: the emitting layer, 151: the emitting auxiliary layer 160: the electron transport layer, 170: the electron injection layer 180: the second electrode(cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be described in detail. Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. Each of these terminologies is not used to define an essence, order or sequence of a corresponding component but used merely to distinguish the corresponding component from other component(s). It should be noted that if a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected or connected to the other component, but another component may be “connected coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as used herein, has a single bond of 1 to 60 carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, as used herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl substituted one or more of carbon atoms consisting of an alkyl with hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as used herein, has double or triple bonds of 2 to 60 carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or “alkyloxy group”, as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group” or “alkenyloxy group”, as used herein, means an oxygen radical attached to an alkenyl group, but is not limited thereto, and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”, as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, as used herein, has 6 to 60 carbon atoms, but is not limited thereto. Herein, the aryl group or arylene group means a monocyclic and polycyclic aromatic group, and may also be formed in conjunction with an adjacent group. Examples of “aryl group” may include a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.

Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl containing one or more of hetero atoms. Unless otherwise stated, the term “heteroaryl group” or “heteroarylene group”, as used herein, means a C2 to C60 aryl containing one or more of hetero atoms or arylene group, but is not limited thereto, and includes at least one of monocyclic and polycyclic rings, and may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein, contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of monocyclic and polycyclic rings, and may include heteroaliphadic ring and/or heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring containing SO₂ instead of carbon consisting of cycle. For example, “heterocyclic group” includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring”, as used herein, means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, is represented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, is represented by —R—O—R′, wherein R or R′ may be independently hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, as used herein, means that substitution is substituted by at least one substituent selected from the group consisting of, but is not limited thereto, deuterium, halogen, an amino group, a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the present invention, as used herein, is applied in the same manner as the substituent definition according to the definition of the exponent of the following Formula.

Here, when a is an integer of 0, it means that the substituent R¹ is absent, that is, when a is 0, it means that all hydrogens are bonded to carbons forming the benzene ring, and in this case, the display of hydrogen bonded to carbon may be omitted and the chemical formula or compound may be described.

When a is an integer of 1, one substituent R¹ is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, they are respectively combined as follows, in which R¹ may be the same as or different from each other, and when a is an integer of 4 to 6, and it is bonded to the carbon of the benzene ring in a similar manner, whereas the indication of hydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present invention and an organic electric element comprising the same will be described.

The present invention provides an organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, wherein the emitting layer comprises a first host compound represented by Formula 1 and a second host compound represented by Formula 2 as the phosphorescent emitting layer:

In Formula 1 and Formula 2,

1) Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶ and Ar⁷ are each independently selected from the group consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si, P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b)), and Ar¹ and Ar², or Ar³ and Ar⁴ may be bonded to each other to form a ring,

2) wherein, L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic, and the R^(a) and R^(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, and P,

3) L¹, L², L³, L⁴ and L⁵ are independently selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; or a C₂-C₆₀ heteroarylene group containing at least one hetero atom of O, N, S, Si, and P;

4) X¹ is O or S,

5) Ring A and B are independently a C₆-C₆₀ aryl group; or a C₂-C₂₀ heterocyclic group,

6) X² is a single bond, N-L⁶-Ar⁷, O, S or CR′R″, wherein R′ and R″ are independently hydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₃-C₆₀ heterocyclic group; or a C₁-C₅₀ alkyl group; R′ and R″ may be bonded to each other to form a spiro ring,

7) X is an integer of 0 to 4, y is an integer of 0 to 3, R^(c) and R^(d) are each independently selected from the group consisting of hydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si and P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a))(R^(b)),

8) wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; siloxane group; boron group; germanium group; cyano group; nitro group; a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination thereof.

Also, the present invention provides an organic electric element, wherein A and B in Formula 1 each independently include a compound represented by any one of the following formulas a-1 to a-7

In Formulas a-1 to a-7,

Z¹ to Z⁴⁸ are each independently CR^(c) or N,

Z¹ to Z⁴⁸ bonded to L¹ to L³ are carbon (C),

R^(c) is the same as the definition of R^(a),

* indicates the position to be condensed.

The present invention provides an organic electric element including a compound wherein L¹ to L⁵ in Formula 1 or Formula 2 are represented by any one of the following Formulas b-1 to b-13:

In Formulas b-1 to b-13,

Y is N-L⁵-Ar⁷, O, S or CR^(d)R^(e),

L⁵ is the same as the definition of L³,

Ar⁷ is the same as the definition of Ar⁵,

R^(d) and R^(e) are the same as the definition of R^(a),

a, c, d and e are each independently an integer of 0 to 4, b is an integer of 0 to 6,

f and g are each independently an integer of 0 to 3, h is an integer of 0 to 2, i is an integer of 0 or 1,

R¹, R² and R³ are each independently hydrogen; deuterium; tritium; halogen; cyano group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L^(a)-N(R^(f))(R^(g)); or in case a, b, c, d, e, f and g are 2 or more, and h is 2 or more, each as plurality are the same as or different from each other, and a plurality of R¹ or a plurality of R² or a plurality of R³ or adjacent R¹ and R², or adjacent R² and R³ may be bonded to each other to form an aromatic or a heteroaromatic ring,

where, L^(a) is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, and P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and C₃-C₆₀ aliphatic hydrocarbon group;

R^(f) and R^(g) are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, and P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, Z⁴⁹, Z⁵⁰, and Z⁵¹ are each independently CR^(h) or N,

at least one of Z⁴⁹, Z⁵⁰, and Z⁵¹ is N,

R^(h) is selected from the group consisting of hydrogen; deuterium; tritium; halogen; cyano group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and adjacent R¹ and R^(h) may be bonded to each other to form an aromatic or a heteroaromatic ring,

The present invention provides a compound wherein the first host compound represented by Formula 1 comprises the compound represented by any one of the following Formulas 3 to Formula 5:

In Formulas 3 to 5,

X¹, A, B, L¹, L², Ar², Ar³ and Ar⁴ are the same as defined above,

C and D are the same as the definition of A,

W is N-L⁷-Ar⁸, O, S, or CR^(i)R^(j)

L⁶ and L⁷ are the same as the definition of L⁴,

Ar⁸ is the same as the definition of Ar⁵,

R^(i) and R^(j) are the same as the definition of R^(a),

The two Ar⁸ are each the same or different, the two W are each the same or different, the two C are each the same or different, the two D are each the same or different.

The present invention provides a compound wherein the first host compound represented by Formula 1 comprises the compound represented by Formula 6:

In Formula 6,

X¹, Ar², Ar³ and Ar⁴ are the same as defined above,

Z¹, Z², Z³ and Z⁴ are each independently CR^(C) or N,

Z¹ to Z⁴ bonded to N is carbon (C),

R^(c) is the same as the definition of R^(a),

W is N-L⁷-Ar⁸, O, S, or CR^(i)R^(j)

L⁷ are the same as the definition of L⁴,

Ar⁸ is the same as the definition of Ar⁵,

R^(i) and R^(j) are the same as the definition of R^(a).

In the present invention, as another example, the first host compound represented by Formula 1 comprises the compound represented by Formula 7 or 8 or 9:

In Formulas 7 to 9,

X¹, Ar², Ar³ and Ar⁴, Z¹, Z², Z³, Z⁴ and W are the same as defined above.

In another aspect, a second host compound represented by Formula 2 comprises a compound represented by any one of Formulas 10 to 13:

In Formulas 10 to 13,

X², L³, L⁴, L⁵, Ar⁵, Ar⁶, R^(c), R^(d), x, y are the same as defined above.

Also, the second host compound represented by Formula 2 comprises a compound represented by Formula 14:

In Formula 14,

1) X², L³, L⁴, L⁵, Ar⁵, R^(C), R^(d), x, y are the same as defined above,

2) X³ is the same as the definition of X²

3) R^(e) and R^(f) are the same as the definition of R^(d) and R^(c),

4) n is the same as the definition of y, m is the same as the definition of x,

The second host compound represented by Formula 2 comprises a compound represented by Formulas 15 to 18:

In Formulas 15 to 18,

X², L³, L⁴, L⁵, Ar⁵, R^(c), R^(d), x, y, X³, R^(e), R^(f), m, n are the same as defined above.

Also, the compound represented by Formula 2 comprises a compound represented by Formula 19:

In Formula 19,

A is the following Formula A-1 or Formula A-2,

X¹¹ and X¹² are each independently O or S,

a′, b′, c′ and d′ are each independently O or 1,

Ar¹¹, Ar¹², Ar¹³ and Ar¹⁴ are each independently C₆-C₁₈ aryl group.

The compound represented by Formula 19 comprises a compound represented by the following Formula 20 or 21:

In Formula 20 and 21,

X¹¹, X¹², a′, b′, c′ and d′ are the same as defined above.

As another example, the compound represented by Formula 2 comprises the compound represented by Formula 22:

These compounds may be used as a first host mixed with a second host such as Bis-carbazole, tertiary amine, and polycyclic heterocyclic compound to be used in the emitting layer.

In Formula 22,

A is the following Formula A-1 or A-2,

Ar¹¹ is a C₆-C₁₈ aryl group,

X¹¹, X¹² and X¹³ are each independently O or S,

m′ and n′ are each independently O or 1,

a′ and c′ each independently an integer of any one of 0 to 5,

d′ is an integer of any one of 0 to 4,

R²¹ is a C₆-C₁₈ aryl group,

Ar¹³ and Ar¹⁴ are each independently a C₆-C₁₈ aryl group.

Also, the compound represented by Formula 22 may be represented by the following Formula 23 or Formula 24.

In Formula 23 and 24,

X¹¹, X¹², X¹³, a′, c′, d′, m′, n′, Ar¹³, Ar¹⁴, R²¹ are the same as defined above.

The compound comprised in Formula 2 may be as a first host mixed with a second host, such as Bis-carbazole, a tertiary amine, and a polycyclic heterocyclic compound to be used in the emitting layer, and more specifically, a compound included in Formula 19 or Formula 22 may be used as the first host mixed with the second host.

As another example, the first host compound represented by Formula 1 comprises Compound 1-1 to Compound 1-175:

As another example, the second host compound represented by Formula 2 comprises the following compounds. That is, Compounds 1′-1 to 1′-84, 2-1 to 2-60, 3-1 to 3-36, P-1 to P-120, 4-1 to 4-12, 5-1 to 5-20, 6-1 to 6-16 and 7-1 to 7-24:

The present invention provides an organic electric element comprising a first electrode, a second electrode, and at least an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, wherein the emitting layer includes a first host represented by Formula 25 and a second host represented by Formula 26:

In Formula 25 and Formula 26,

1) Ar²¹, Ar²², Ar²³ and Ar²⁴ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si, P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;

2) R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are each the same or different, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; or in case a1, a2, a3, a4, b1, b2, b3 and b4 are 2 or more, each as plurality are the same as or different from each other, and a plurality of R³¹ or a plurality of R³² or a plurality of R³³ or a plurality of R³⁴ or a plurality of R³⁵ or a plurality of R³⁶ or a plurality of R³⁷ or a plurality of R³⁸ may be bonded to each other to form an aromatic or a heteroaromatic ring,

3) a1, a2, a3, a4, b2 and b3 are each independently an integer of 0 to 3, b1 and b4 are each independently an integer of 0 to 4,

4) X²¹ and X²² are each independently O or S,

5) B is a substituent represented by Formula 27,

In Formula 27,

6) R³⁹ and R⁴⁰ are the same as the definition of R³¹,

7) Ar²⁵ is the same as the definition of Ar²¹,

8) X²³ is O or S,

10) b5 and b6 are each independently an integer of 0 to 3, and

11)

means the bonding position,

wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group; siloxane group; boron group; germanium group; cyano group; nitro group; a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxy group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination thereof.

Also, the present invention provides an organic electric element comprising a compound represented by any one of Formulas 25-1 to 25-4:

In Formulas 25-1 to 25-4,

R³¹, R³², R³³, R³⁴, a1, a2, a3, a4, Ar²¹, Ar²², Ar²³, X²¹ and X²² are the same as defined above,

The present invention also provides an organic electric element comprising a compound wherein Ar²¹, Ar²² and Ar²³ of Formula 25 are any one of the following Formulas Ar-1 to Ar-12:

In Formulas Ar-1 to Ar-12,

1) Z⁶¹, Z⁶², Z⁶³, Z⁶⁴ and Z⁶⁵ are each independently CR⁴⁶ or N, with the proviso that at least one of Z⁶¹, Z⁶², Z⁶³, Z⁶⁴ and Z⁶⁵ is N,

2) X²⁴ is O, S, CR⁴⁹R⁵⁰ or NR⁵¹

3) R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁶ are the same as the definition of R³¹,

4) R⁴⁹, R⁵⁰ and R⁵¹ are each independently selected from the group consisting of hydrogen; deuterium; C₁-C₆₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; a C₁-C₅₀ alkoxy group; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si, P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and R⁴⁹ and R⁵⁰ may be bonded to each other to form a spiro,

5) c1 is an integer of 0 to 5, c2, c5, c6 and c7 are each independently an integer of 0 to 4, c3 is an integer of 0 to 7, c4 is an integer of 0 to 3,

6)

means the bonding position.

As other examples, the compound represented by Formula 25 comprises Compound 7-10 to Compound 7-20 and Compound 8-1 to Compound 8-38:

In one aspect of the present invention relating to the organic electric element comprising a compound of Formula 25 and a compound of Formula 26, the substituent B in Formula 26 is any one of the following Formulas 27-1 to 27-4:

In Formulas 27-1 to 27-4,

1) R³⁹, R⁴⁰, X²³, Ar²⁵, b5 and b6 are the same as defined above,

2)

means the bonding position.

In another aspect of the present invention relating to the organic electric element comprising a compound of Formula 25 and compound of Formula 26, the substituent B of Formula 26 is any one of the following Formulas 27-5 to 27-12:

In Formulas 27-5 to 27-12,

1) R³⁹, R⁴⁰, X²³, Ar²⁵, b5 and b6 are the same as defined above,

2)

means the bonding position.

Other non-limiting examples of the compound of Formula 26 comprise Compound 9-1 to Compound 9-36:

Referring to FIGURE, the organic electric element(100) according to the present invention includes a first electrode(120) formed on a substrate(110), a second electrode(180), and an organic material layer including the compound represented by Formula 1 between the first electrode(120) and the second electrode(180). Here, the first electrode(120) may be an anode (positive electrode), and the second electrode(180) may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer(130), a hole transport layer(140), an emitting layer(150), an emitting-auxiliary layer(151), an electron transport layer(160), and an electron injection layer(170) formed in sequence on the first electrode(120). Here, the remaining layers except the emitting layer(150) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer(151), an electron transport auxiliary layer, a buffer layer(141), etc., and the electron transport layer(160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to the present invention may further include a protective layer formed on at least one side of the first and second electrodes, which is a side opposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electrical characteristics, the interface characteristics, and the like may vary depending on which substituent is bonded at which position, therefore the choice of core and the combination of sub-substituents associated therewith is also very important, and in particular, when the optimal combination of energy levels and T1 values and unique properties of materials(mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long lifespan and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and after forming an organic material layer including the hole injection layer(130), the hole transport layer(140), the emitting layer(150), the electron transport layer(160) and the electron injection layer(170) thereon, the organic electroluminescent device according to an embodiment of the present invention can be manufactured by depositing a material that can be used as a cathode thereon.

In addition, an emission auxiliary layer(151) may be further formed between the hole transport layer(140) and the emitting layer(150), and an electron transport auxiliary layer may be further formed between the emitting layer(150) and the electron transport layer (160).

Accordingly, the present invention includes at least one hole transport layer between the first electrode and the emitting layer, wherein the hole transport layer includes a hole transport layer, an emitting auxiliary layer, or both, and wherein the hole transport layer includes the compound represented by Formula 1.

Also, the compounds represented by Formula 1 and by Formula 2 are mixed in a ratio of any one of 1:9 to 9:1 to be included in the emitting layer, preferably mixed in a ratio of 1:9 to 5:5, more preferably in a ratio of 2:8 or 3:7 to be included in the emitting layer.

The present invention may further include a light efficiency-enhancing layer formed on either or both sides of the first electrode and the second electrode, the side being located opposite to the organic material layer and not facing the organic material layer. Also, the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

The organic electric element according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and excellent processability, while there is an advantage that can be manufactured using the existing LCD color filter technology. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, R(Red), G(Green), B(Blue) light emitting parts are arranged in a side-by-side manner, and R, G, B light emitting layers are stacked up and down, and blue (B) electroluminescence by organic emitting layer and, there is a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor using light from this, and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising a display device including the organic electric element; and a control unit for driving the display device. According to one aspect, the present invention provides an electronic device wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and an element for monochromic or white illumination. At this time, the electronic device may be a current or future wired/wireless communication terminal, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant(PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula 1 and Formula 2 according to the present invention and preparation examples of the organic electric element of the present invention will be described in detail by way of examples, but are not limited to the following examples of the invention.

Synthesis Example 1

The final product 1 represented by Formula 1 of the present invention can be synthesized by reaction between Sub 1 and Sub 2 as illustrated in the following Reaction Scheme 1, but is not limited thereto. X¹, A, B, L¹, L², Ar¹ to Ar⁴ are the same as defined in Formula 1, and Hal¹ is Br or Cl.

I. Synthesis Examples of Sub 1

Sub 1 of Reaction Scheme 1 is synthesized by the reaction path of Reaction Scheme 2 below, but is not limited thereto.

1. Synthesis Examples of Sub 1-1

Starting material Sub 2-1 (15.22 g, 89.94 mmol) was added in a round bottom flask and dissolved in toluene (750 mL), Sub 1-1-c (CAS Registry Number: 669773-34-6) (46.14 g, 134.91 mmol), Pd₂(dba)₃ (2.47 g, 2.70 mmol), P(t-Bu)₃ (1.46 g, 7.19 mmol), NaOt-Bu (25.93 g, 269.81 mmol) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 23.61 g of the product. (yield: 61%)

2. Synthesis Examples of Sub 1-3

To the starting material Sub 2-12 (13.94 g, 63.57 mmol), Sub 1-3-e (CAS Registry Number: 201138-91-2) (31.08 g, 95.35 mmol), Pd₂(dba)₃ (1.75 g, 1.91 mmol) P(t-Bu)₃ (1.03 g, 5.09 mmol), NaOt-Bu (18.33 g, 190.71 mmol), toluene (530 ml) were added, the same procedure as described in the synthesis method of Sub 1-1 was carried out to obtain 19.78 g of the product. (yield: 67%).

3. Synthesis Examples of Sub 1-5

(1) Synthesis of Sub 1-5-a

Starting material (2-bromo-6-iodophenyl)(ethyl)sulfane (9.94 g, 28.98 mmol) was added in a round bottom flask and dissolved in THE (100 mL), (4-chlorophenyl)boronic acid (4.53 g, 28.98 mmol), Pd(PPh₃)₄ (1.00 g, 0.87 mmol), NaOH (2.32 g, 57.96 mmol), water (50 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 8.55 g of the product. (yield: 90%)

(2) Synthesis of Sub 1-5-b

To Sub 1-5-a (8.55 g, 26.09 mmol) obtained in the above synthesis, acetic acid (90 ml) was added, 35% hydrogen peroxide (H₂O₂) (2.66 g, 78.28 mmol) was added and stirred at room temperature. When the reaction was completed, after neutralization with NaOH aqueous solution, extraction was performed with EA and washed with water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography to obtain 8.70 g of the product. (yield: 97%)

(3) Synthesis of Sub 1-5-c

To Sub 1-5-b (8.70 g, 25.32 mmol) obtained in the above synthesis, sulfuric acid (H2SO4) (50 ml) was added and stirred at room temperature. When the reaction was completed, after neutralization with NaOH aqueous solution, extraction was performed with MC and washed with water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography to obtain 7.16 g of the product. (yield: 95%)

(4) Synthesis of Sub 1-5

The obtained Sub 1-5-c (7.16 g, 24.06 mmol) was added in a round bottom flask and dissolved in toluene (240 mL), Sub 2-11 (5.28 g, 24.06 mmol), Pd₂(dba)₃ (0.66 g, 0.72 mmol), P(t-Bu)₃ (0.49 g, 2.41 mmol), NaOt-Bu (4.62 g, 48.12 mmol) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 8.08 g of the product. (yield: 77%)

4. Synthesis Examples of Sub 1-17

(1) Synthesis of Sub 1-17-a

In the starting material (4-bromo-2-iodophenyl)(ethyl)sulfane (10.65 g, 31.05 mmol), (4-chloro-[1,1′-biphenyl]-2-yl)boronic acid (7.22 g, 31.05 mmol)), Pd(PPh3)4 (1.08 g, 0.93 mmol), NaOH (2.48 g, 62.10 mmol), THE (100 ml), water (50 ml) were added, and the same procedure as described in the synthesis method of Sub 1-5-a was carried out to obtain 9.90 g of the product. (yield: 79%).

(2) Synthesis of Sub 1-17-b

Sub 1-17-a (9.90 g, 24.52 mmol), acetic acid (80 ml), 35% hydrogen peroxide (H₂O₂) (2.50 g, 73.56 mmol) obtained in the above synthesis were used in the synthesis method of Sub 1-5-b. Thus, the product 9.78 g (yield: 95%) was obtained.

(3) Synthesis of Sub 1-17-c

Sub 1-17-b (9.78 g, 23.30 mmol) and sulfuric acid (H2SO4) (50 ml) obtained in the above synthesis were used in the synthesis method of Sub 1-5-c. Thus, the product 7.84 g (yield: 90%) was obtained.

(4) Synthesis of Sub 1-17

To Sub 1-17-c (7.84 g, 20.98 mmol) obtained in the above synthesis, Sub 2-78 (7.02 g, 20.98 mmol), Pd₂(dba)3 (0.58 g, 0.63 mmol) P(t-Bu)3 (0.42 g, 2.10 mmol), NaOt-Bu (4.03 g, 41.96 mmol), and toluene (210 ml) were added, and the same procedure as described in the synthesis method of Sub 1-5 was carried out to obtain 10.79 g of the product. (Yield: 82%).

5. Synthesis Examples of Sub 1-82

In the starting material Sub 2-1 (16.48 g, 97.38 mmol), Sub 1-82-c (CAS Registry Number: 83834-10-0) (49.96 g, 146.07 mmol), Pd₂(dba)3 (2.68 g, 2.92 mmol) P(t-Bu)3 (1.58 g, 7.79 mmol), NaOt-Bu (28.08 g, 292.15 mmol), toluene (810 ml) were added and the same procedure as described in the synthesis method of Sub 1-1 was carried out to obtain 26.40 g of the product. (Yield: 63%).

6. Synthesis Examples of Sub 1-102

(1) Synthesis of Sub 1-102-d

In the starting material 4-bromo-2-iodophenol (39.85 g, 133.32 mmol), (2-chlorophenyl)boronic acid (20.85 g, 133.32 mmol), Pd(PPh₃)₄ (4.62 g, 4.00 mmol), NaOH (10.67 g, 266.64 mmol), THE (440 ml), water (220 ml) were added and the same procedure as described in the synthesis method of Sub 1-5-a was carried out to obtain 28.73 g of the product. (Yield: 76%).

(2) Synthesis of Sub 1-102-e

To Sub 1-102-d (28.73 g, 101.32 mmol) obtained in the above synthesis, Pd(OAc)₂ (2.27 g, 10.13 mmol), 3-nitropyridine (1.26 g, 10.13 mmol), BzOOtBu (tert-butyl peroxybenzoate) (39.36 g, 202.65 mmol), C₆F₆ (hexafluorobenzene) (150 ml), DMI (N,N′-dimethylimidazolidinone) (100 ml) were added and refluxed at 90° C. for 3 hours. When the reaction is completed, the temperature of the reaction product is cooled to room temperature, extracted with EA, and washed with water. The organic layer was dried over MgSO₄ and concentrated, and the resulting organic material was separated using a silicagel column to obtain 13.69 g (48%) of the product.

(3) Synthesis of Sub 1-102

To Sub 1-102-e (13.69 g, 48.63 mmol) obtained in the above synthesis, Sub 2-29 (13.39 g, 48.63 mmol), Pd₂(dba)₃ (1.34 g, 1.46 mmol) P(t-Bu)₃ (0.98 g, 4.86 mmol), NaOt-Bu (9.35 g, 97.25 mmol), toluene (490 ml) were added, and the same procedure as described in the synthesis method of Sub 1-5 was carried out to obtain 19.67 g of the product. (Yield: 85%).

7. Synthesis Examples of Sub 1-104

In the starting material Sub 2-1 (9.15 g, 54.04 mmol), Sub 1-104-c (CAS Registry Number: 31574-87-5) (27.73 g, 81.07 mmol), Pd₂(dba)₃ (1.48 g, 1.62 mmol) P(t-Bu)₃ (0.87 g, 4.32 mmol), NaOt-Bu (15.58 g, 162.13 mmol), toluene (450 ml) were added and the same procedure as described in the synthesis method of Sub 1-1 was carried out to obtain 15.12 g of the product. (Yield: 65%).

8. Synthesis Examples of Sub 1-112

(1) Synthesis of Sub 1-112-a

In the starting material (3-bromo-2-iodophenyl)(ethyl)sulfane (12.73 g, 37.11 mmol), (2-chlorophenyl)boronic acid (5.80 g, 37.11 mmol), Pd(PPh₃)₄ (1.29 g, 1.11 mmol), NaOH (2.97 g, 74.22 mmol), THE (120 ml), water (60 ml) were added and the same procedure as described in the synthesis method of Sub 1-5-a was carried out to obtain 9.48 g of the product. (Yield: 78%).

(2) Synthesis of Sub 1-112-b

Sub 1-112-a (9.48 g, 28.93 mmol) obtained in the above synthesis, acetic acid (95 ml), 35% hydrogen peroxide (H₂O₂) (2.95 g, 86.80 mmol) were added, and the same procedure as described in the synthesis method of Sub 1-5-b was carried out to obtain 9.74 g of the product. (Yield: 98%).

(3) Synthesis of Sub 1-112-c

Sub 1-112-b (9.74 g, 28.34 mmol), sulfuric acid (H2SO4) (60 ml) obtained in the above synthesis were added, and the same procedure as described in the synthesis method of Sub 1-5-c was carried out to obtain 7.76 g of the product. (Yield: 92%).

(4) Synthesis of Sub 1-112

To Sub 1-112-c (7.76 g, 26.08 mmol) obtained in the above synthesis, Sub 2-1 (4.41 g, 26.08 mmol), Pd₂(dba)₃ (0.72 g, 0.78 mmol) P(t-Bu)₃ (0.53 g, 2.61 mmol), NaOt-Bu (5.01 g, 52.15 mmol), toluene (260 ml) were added, and the same procedure as described in the synthesis method of Sub 1-5 was carried out to obtain 5.84 g of the product. (Yield: 58%).

The compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1.

TABLE 1 compound FD-MS Sub 1-1 m/z = 429.02(C₂₄H₁₆BrNS = 430.36) Sub 1-2 m/z = 413.04(C₂₄H₁₆BrNO = 414.30) Sub 1-3 m/z = 463.06(C₂₈H₁₈BrNO = 464.36) Sub 1-4 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-5 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-6 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-7 m/z = 551.11(C₃₆H₂₂ClNOS = 552.09) Sub 1-8 m/z = 501.13(C₃₃H₂₄ClNS = 502.07) Sub 1-9 m/z = 445.12(C₃₀H₂₀ClNO = 445.95) Sub 1-10 m/z = 445.12(C₃₀H₂₀ClNO = 445.95) Sub 1-11 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-12 m/z = 491.06(C₃₀H₁₈ClNS₂ = 492.05) Sub 1-13 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-14 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-15 m/z = 575.11(C₃₈H₂₂ClNOS = 576.11) Sub 1-16 m/z = 552.11(C₃₅H₂₁ClN₂OS = 553.08) Sub 1-17 m/z = 626.16(C₄₂H₂₇ClN₂S = 627.20) Sub 1-18 m/z = 643.12(C₄₂H₂₆ClNS₂ = 644.25) Sub 1-19 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-20 m/z = 369.09(C₂₄H₁₆ClNO = 369.85) Sub 1-21 m/z = 475.08(C₃₀H₁₈ClNOS = 475.99) Sub 1-22 m/z = 565.09(C₃₆H₂₀ClNO₂S = 566.07) Sub 1-23 m/z = 519.14(C₃₆H₂₂ClNO = 520.03) Sub 1-24 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-25 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-26 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-27 m/z = 597.04(C₃₆H₂₀ClNS₃ = 598.19) Sub 1-28 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-29 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-30 m/z = 485.10(C₃₂H₂₀ClNS = 486.03) Sub 1-31 m/z = 591.14(C₃₉H₂₆ClNOS = 592.15) Sub 1-32 m/z = 559.13(C₃₈H₂₂ClNO₂ = 560.05) Sub 1-33 m/z = 677.16(C₄₆H₂₈ClNOS = 678.25) Sub 1-34 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-35 m/z = 399.08(C₂₅H₁₈ClNS = 399.94) Sub 1-36 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-37 m/z = 461.10(C₃₀H₂₀ClNS = 462.01) Sub 1-38 m/z = 511.12(C₃₄H₂₂ClNS = 512.07) Sub 1-39 m/z = 399.08(C₂₅H₁₈ClNS = 399.94) Sub 1-40 m/z = 461.10(C₃₀H₂₀ClNS = 462.01) Sub 1-41 m/z = 491.06(C₃₀H₁₈ClNS₂ = 492.05) Sub 1-42 m/z = 491.06(C₃₀H₁₈ClNS₂ = 492.05) Sub 1-43 m/z = 491.06(C₃₀H₁₈ClNS₂ = 492.05) Sub 1-44 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-45 m/z = 643.12(C₄₂H₂₆ClNS₂ = 644.25) Sub 1-46 m/z = 607.12(C₃₉H₂₆ClNS₂ = 608.21) Sub 1-47 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-48 m/z = 475.08(C₃₀H₁₈ClNOS = 475.99) Sub 1-49 m/z = 626.16(C₄₂H₂₇ClN₂S = 627.20) Sub 1-50 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-51 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-52 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-53 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-54 m/z = 555.09(C₃₅H₂₂ClNS₂ = 556.14) Sub 1-55 m/z = 525.10(C₃₄H₂₀ClNOS = 526.05) Sub 1-56 m/z = 513.13(C₃₄H₂₄ClNS = 514.08) Sub 1-57 m/z = 485.10(C₃₂H₂₀ClNS = 486.03) Sub 1-58 m/z = 537.13(C₃₆H₂₄ClNS = 538.11) Sub 1-59 m/z = 626.16(C₄₂H₂₇ClN₂S = 627.20) Sub 1-60 m/z = 369.09(C₂₄H₁₆ClNO = 369.85) Sub 1-61 m/z = 445.12(C₃₀H₂₀ClNO = 445.95) Sub 1-62 m/z = 495.14(C₃₄H₂₂ClNO = 496.01) Sub 1-63 m/z = 459.10(C₃₀H₁₈ClNO₂ = 459.93) Sub 1-64 m/z = 534.15(C₃₆H₂₃ClN₂O = 535.04) Sub 1-65 m/z = 535.17(C₃₇H₂₆ClNO = 536.07) Sub 1-66 m/z = 525.10(C₃₄H₂₀ClNOS = 526.05) Sub 1-67 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-68 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-69 m/z = 461.10(C₃₀H₂₀ClNS = 462.01) Sub 1-70 m/z = 611.15(C₄₂H₂₆ClNS = 612.19) Sub 1-71 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-72 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-73 m/z = 475.08(C₃₀H₁₈ClNOS = 475.99) Sub 1-74 m/z = 551.11(C₃₆H₂₂ClNOS = 552.09) Sub 1-75 m/z = 591.14(C₃₉H₂₆ClNOS = 592.15) Sub 1-76 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-77 m/z = 591.09(C₃₈H₂₂ClNS₂ = 592.17) Sub 1-78 m/z = 537.13(C₃₆H₂₄ClNS = 538.11) Sub 1-79 m/z = 379.15(C₂₄H₆D₁₀ClNO = 379.91) Sub 1-80 m/z = 459.10(C₃₀H₁₈ClNO₂ = 459.93) Sub 1-81 m/z = 445.12(C₃₀H₂₀ClNO = 445.95) Sub 1-82 m/z = 429.02(C₂₄H₁₆BrNS = 430.36) Sub 1-83 m/z = 443.03(C₂₅H₁₈BrNS = 444.39) Sub 1-84 m/z = 479.03(C₂₈H₁₈BrNS = 480.42) Sub 1-85 m/z = 485.10(C₃₂H₂₀ClNS = 486.03) Sub 1-86 m/z = 545.12(C₃₄H₂₄ClNO₂S = 546.08) Sub 1-87 m/z = 413.04(C₂₄H₁₆BrNO = 414.30) Sub 1-88 m/z = 529.10(C₃₃H₂₄BrNO = 530.47) Sub 1-89 m/z = 589.10(C₃₈H₂₄BrNO = 590.52) Sub 1-90 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-91 m/z = 537.13(C₃₆H₂₄ClNS = 538.11) Sub 1-92 m/z = 491.06(C₃₀H₁₈ClNS₂ = 492.05) Sub 1-93 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-94 m/z = 567.09(C₃₆H₂₂ClNS₂ = 568.15) Sub 1-95 m/z = 551.11(C₃₆H₂₂ClNOS = 552.09) Sub 1-96 m/z = 683.15(C₄₅H₃₀ClNS₂ = 684.31) Sub 1-97 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-98 m/z = 591.09(C₃₈H₂₂ClNS₂ = 592.17) Sub 1-99 m/z = 748.18(C₄₉H₃₃ClN₂S₂ = 749.39) Sub 1-100 m/z = 369.09(C₂₄H₁₆ClNO = 369.85) Sub 1-101 m/z = 419.11(C₂₈H₁₈ClNO = 419.91) Sub 1-102 m/z = 475.08(C₃₀H₁₈ClNOS = 475.99) Sub 1-103 m/z = 625.13(C₄₂H₂₄ClNOS = 626.17) Sub 1-104 m/z = 429.02(C₂₄H₁₆BrNS = 430.36) Sub 1-105 m/z = 479.03(C₂₈H₁₈BrNS = 480.42) Sub 1-106 m/z = 505.05(C₃₀H₂₀BrNS = 506.46) Sub 1-107 m/z = 435.08(C₂₈H₁₈ClNS = 435.97) Sub 1-108 m/z = 541.07(C₃₄H₂₀ClNS₂ = 542.11) Sub 1-109 m/z = 489.07(C₃₀H₂₀BrNO = 490.40) Sub 1-110 m/z = 565.10(C₃₆H₂₄BrNO = 566.50) Sub 1-111 m/z = 716.15(C₄₇H₂₉BrN₂O = 717.67) Sub 1-112 m/z = 385.07(C₂₄H₁₆ClNS = 385.91) Sub 1-113 m/z = 511.12(C₃₄H₂₂ClNS = 512.07) Sub 1-114 m/z = 557.14(C₃₅H₂₈ClNSSi = 558.21) Sub 1-115 m/z = 495.14(C₃₄H₂₂ClNO = 496.01) Sub 1-116 m/z = 575.11(C₃₈H₂₂ClNOS = 576.11) Sub 1-117 m/z = 469.12(C₃₂H₂₀ClNO = 469.97) Sub 1-118 m/z = 469.12(C₃₂H₂₀ClNO = 469.97) Sub 1-119 m/z = 635.17(C₄₄H₂₈ClNO₂ = 636.15) Sub 1-120 m/z = 650.16(C₄₄H₂₇ClN₂S = 651.22) Sub 1-121 m/z = 585.13(C₄₀H₂₄ClNS = 586.15)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 3 may be synthesized (initiated in Korean Patent Registration No. 10-1251451 (registered on Apr. 5, 2013) of the applicant) by the reaction path of Reaction Scheme 3 below, but is not limited thereto.

Z¹ is Ar¹ or Ar³, Z² is Ar² or Ar⁴.

The compounds belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 2.

TABLE 2 compound FD-MS Sub 2-1 m/z = 169.09(C₁₂H₁₁N = 169.23) Sub 2-2 m/z = 183.10(C₁₃H₁₃N = 183.25) Sub 2-3 m/z = 183.10(C₁₃H₁₃N = 183.25) Sub 2-4 m/z = 187.08(C₁₂H₁₀FN = 187.22) Sub 2-5 m/z = 194.08(C₁₃H₁₀N₂ = 194.24) Sub 2-6 m/z = 197.12(C₁₄H₁₅N = 197.28) Sub 2-7 m/z = 241.13(C₁₅H₁₉NSi = 241.41) Sub 2-8 m/z = 229.11(C₁₄H₁₅NO₂ = 229.28) Sub 2-9 m/z = 174.12(C₁₂H₆D₅N = 174.26) Sub 2-10 m/z = 179.15(C₁₂HD₁₀N = 179.29) Sub 2-11 m/z = 219.10(C₁₆H₁₃N = 219.29) Sub 2-12 m/z = 219.10(C₁₆H₁₃N = 219.29) Sub 2-13 m/z = 269.12(C₂₀H₁₅N = 269.35) Sub 2-14 m/z = 245.12(C₁₈H₁₅N = 245.33) Sub 2-15 m/z = 250.15(C₁₈H₁₀D₅N = 250.36) Sub 2-16 m/z = 245.12(C₁₈H₁₅N = 245.33) Sub 2-17 m/z = 269.12(C₂₀H₁₅N = 269.35) Sub 2-18 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub 2-19 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub 2-20 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub 2-21 m/z = 295.14(C₂₂H₁₇N = 295.39) Sub 2-22 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub 2-23 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub 2-24 m/z = 397.18(C₃₀H₂₃N = 397.52) Sub 2-25 m/z = 295.14(C₂₂H₁₇N = 295.39) Sub 2-26 m/z = 295.14(C₂₂H₁₇N = 295.39) Sub 2-27 m/z = 345.15(C₂₆H₁₉N = 345.45) Sub 2-28 m/z = 395.17(C₃₀H₂₁N = 395.51) Sub 2-29 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-30 m/z = 289.09(C₁₉H₁₅NS = 289.40) Sub 2-31 m/z = 293.07(C₁₈H₁₂FNS = 293.36) Sub 2-32 m/z = 289.09(C₁₉H₁₅NS = 289.40) Sub 2-33 m/z = 289.09(C₁₉H₁₅NS = 289.40) Sub 2-34 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-35 m/z = 365.12(C₂₅H₁₉NS = 365.49) Sub 2-36 m/z = 367.10(C₂₄H₁₇NOS = 367.47) Sub 2-37 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-38 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-39 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-40 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub 2-41 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub 2-42 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-43 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-44 m/z = 359.13(C₂₆H₁₇NO = 359.43) Sub 2-45 m/z = 409.15(C₃₀H₁₉NO = 409.49) Sub 2-46 m/z = 336.13(C₂₃H₁₆N₂O = 336.39) Sub 2-47 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-48 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-49 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-50 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub 2-51 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub 2-52 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-53 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-54 m/z = 411.16(C₃₀H₂₁NO = 411.50) Sub 2-55 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-56 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-57 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub 2-58 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub 2-59 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-60 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-61 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-62 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-63 m/z = 427.14(C₃₀H₂₁NS = 427.57) Sub 2-64 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub 2-65 m/z = 381.06(C₂₄H₁₅NS₂ = 381.51) Sub 2-66 m/z = 457.10(C₃₀H₁₉NS₂ = 457.61) Sub 2-67 m/z = 349.11(C₂₄H₁₅NO₂ = 349.39) Sub 2-68 m/z = 349.11(C₂₄H₁₅NO₂ = 349.39) Sub 2-69 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-70 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-71 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-72 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-73 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-74 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-75 m/z = 435.16(C₃₂H₂₁NO = 435.53) Sub 2-76 m/z = 309.12(C₂₂H₁₅NO = 309.37) Sub 2-77 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-78 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 2-79 m/z = 410.18(C₃₀H₂₂N₂ = 410.52) Sub 2-80 m/z = 440.13(C₃₀H₂₀N₂S = 440.56) Sub 2-81 m/z = 436.19(C₃₂H₂₄N₂ = 436.56) Sub 2-82 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 2-83 m/z = 410.18(C₃₀H₂₂N₂ = 410.52) Sub 2-84 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 2-85 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 2-86 m/z = 285.15(C₂₁H₁₉N = 285.39) Sub 2-87 m/z = 361.18(C₂₇H₂₃N = 361.49) Sub 2-88 m/z = 285.15(C₂₁H₁₉N = 285.39) Sub 2-89 m/z = 435.20(C₃₃H₂₅N = 435.57) Sub 2-90 m/z = 335.17(C₂₅H₂₁N = 335.45) Sub 2-91 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 2-92 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 2-93 m/z = 375.16(C₂₇H₂₁NO = 375.47) Sub 2-94 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub 2-95 m/z = 409.18(C₃₁H₂₃N = 409.53) Sub 2-96 m/z = 407.17(C₃₁H₂₁N = 407.52) Sub 2-97 m/z = 513.16(C₃₇H₂₃NS = 513.66) Sub 2-98 m/z = 457.18(C₃₅H₂₃N = 457.58) Sub 2-99 m/z = 225.06(C₁₄H₁₁NS = 225.31)

III. Synthesis of Final Product

After dissolving Sub 1 (1 eq.) with Toluene in a round bottom flask, Sub 2 (1 eq.), Pd₂(dba)3 (0.03 eq.), (t-Bu)3P (1.00 eq.), and NaOt-Bu (2 eq.) were stirred at 100° C. When the reaction was completed, the resulting compound was extracted with CH₂Cl₂ and water, and the organic layer was dried over MgSO₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain Final product 1.

The Compounds of the present invention 1-30, 1-32, 1-35, 1-37, 1-67, 1-80, 1-86, 1-94, 1-111. 1-119, 1-133 are manufactured by the synthesis method disclosed in Korean Patent Registration No. 10-1668448 (registered on Oct. 17, 2016) and Korean Patent Registration No. 10-1789998 (registered on Oct. 19, 2017) of the applicant.

1. Synthesis Example of 1-1

The obtained Sub 1-1 (5.97 g, 13.87 mmol) was added in a round bottom flask and dissolved in toluene (140 mL), Sub 2-17 (3.74 g, 13.87 mmol), Pd₂(dba)₃ (0.38 g, 0.42 mmol), P(t-Bu)₃ (0.28 g, 1.39 mmol), NaOt-Bu (2.67 g, 27.74 mmol) were added and stirred at 100° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 6.09 g of the product. (Yield: 71%)

2. Synthesis Example of 1-2

To Sub 1-1 (5.29 g, 12.29 mmol) obtained in the above synthesis, Sub 2-37 (4.32 g, 12.29 mmol), Pd₂(dba)₃ (0.34 g, 0.37 mmol) P(t-Bu)₃ (0.25 g, 1.23 mmol), NaOt-Bu (2.36 g, 24.58 mmol), toluene (125 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 6.81 g of the product. (Yield: 79%).

3. Synthesis Example of 1-4

To Sub 1-3 (6.13 g, 13.20 mmol) obtained in the above synthesis, Sub 2-41 (4.08 g, 13.20 mmol), Pd₂(dba)₃ (0.36 g, 0.40 mmol) P(t-Bu)₃ (0.27 g, 1.32 mmol), NaOt-Bu (2.54 g, 26.40 mmol), toluene (130 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 7.32 g of the product. (Yield: 80%).

4. Synthesis Example of 1-10

To Sub 1-5 (5.56 g, 12.75 mmol) obtained in the above synthesis, Sub 2-43 (4.28 g, 12.75 mmol), Pd₂(dba)₃ (0.35 g, 0.38 mmol) P(t-Bu)₃ (0.26 g, 1.28 mmol), NaOt-Bu (2.45 g, 25.51 mmol), toluene (130 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 8.06 g of the product. (Yield: 86%).

5. Synthesis Example of 1-24

To Sub 1-17 (6.18 g, 9.85 mmol) obtained in the above synthesis, Sub 2-1 (1.67 g, 9.85 mmol), Pd₂(dba)₃ (0.27 g, 0.30 mmol) P(t-Bu)₃ (0.20 g, 0.99 mmol), NaOt-Bu (1.89 g, 19.71 mmol), toluene (100 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 5.62 g of the product. (Yield: 75%).

6. Synthesis Example of 1-122

To Sub 1-82 (5.05 g, 11.73 mmol) obtained in the above synthesis, Sub 2-49 (4.12 g, 11.73 mmol), Pd₂(dba)₃ (0.32 g, 0.35 mmol) P(t-Bu)₃ (0.24 g, 1.17 mmol), NaOt-Bu (2.26 g, 23.47 mmol), toluene (120 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 7.65 g of the product. (Yield: 93%).

7. Synthesis Example of 1-125

To Sub 1-82 (5.20 g, 12.08 mmol) obtained in the above synthesis, Sub 2-40 (3.13 g, 12.08 mmol), Pd₂(dba)₃ (0.33 g, 0.36 mmol) P(t-Bu)₃ (0.24 g, 1.21 mmol), NaOt-Bu (2.32 g, 24.17 mmol), toluene (120 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 6.69 g of the product. (Yield: 91%).

8. Synthesis Example of 1-141

To Sub 1-102 (6.26 g, 13.15 mmol) obtained in the above synthesis, Sub 2-1 (2.23 g, 13.15 mmol), Pd₂(dba)₃ (0.36 g, 0.39 mmol) P(t-Bu)₃ (0.27 g, 1.32 mmol), NaOt-Bu (2.53 g, 26.30 mmol), toluene (130 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 6.57 g of the product. (Yield: 82%).

9. Synthesis Example of 1-146

To Sub 1-104 (6.12 g, 14.22 mmol) obtained in the above synthesis, Sub 2-83 (5.84 g, 14.22 mmol), Pd₂(dba)₃ (0.39 g, 0.43 mmol) P(t-Bu)₃ (0.29 g, 1.42 mmol), NaOt-Bu (2.73 g, 28.43 mmol), toluene (140 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 8.00 g of the product. (Yield: 74%).

10. Synthesis Example of 1-158

To Sub 1-112 (5.75 g, 14.90 mmol) obtained in the above synthesis, Sub 2-29 (4.10 g, 14.90 mmol), Pd₂(dba)₃ (0.41 g, 0.45 mmol) P(t-Bu)₃ (0.30 g, 1.49 mmol), NaOt-Bu (2.86 g, 29.80 mmol), toluene (150 ml) were added, and the same procedure as described in the synthesis method of 1-1 was carried out to obtain 6.24 g of the product. (Yield: 67%).

Meanwhile, FD-MS values of compounds 1-1 to 1-175 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.

TABLE 3 compound FD-MS 1-1 m/z = 618.21(C₄₄H₃₀N₂S = 618.80) 1-2 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-3 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-4 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 1-5 m/z = 742.30(C₅₅H₃₈N₂O = 742.92) 1-6 m/z = 654.27(C₄₈H₃₄N₂O = 654.81) 1-7 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-8 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 1-9 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 1-10 m/z = 734.24(C₅₂H₃₄N₂OS = 734.92) 1-11 m/z = 872.32(C₆₄H₄₄N₂S = 873.13) 1-12 m/z = 718.26(C₅₂H₃₄N₂O₂ = 718.86) 1-13 m/z = 568.20(C₄₀H₂₈N₂S = 568.74) 1-14 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-15 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 1-16 m/z = 730.30(C₅₄H₃₈N₂O = 730.91) 1-17 m/z = 698.20(C₄₈H₃₀N₂O₂S = 698.84) 1-18 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-19 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-20 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-21 m/z = 750.22(C₅₂H₃₄N₂S₂ = 750.98) 1-22 m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.02) 1-23 m/z = 867.24(C₅₉H₃₇N₃OS₂ = 868.09) 1-24 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 1-25 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-26 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-27 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 1-28 m/z = 894.20(C₆₀H₃₄N₂O₃S₂ = 895.06) 1-29 m/z = 618.21(C₄₄H₃₀N₂S = 618.80) 1-30 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-31 m/z = 780.17(C₅₂H₃₂N₂S₃ = 781.02) 1-32 m/z = 734.24(C₅₂H₃₄N₂OS = 734.92) 1-33 m/z = 834.31(C₆₁H₄₂N₂S = 835.08) 1-34 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-35 m/z = 724.25(C₅₁H₃₆N₂OS = 724.92) 1-36 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-37 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-38 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-39 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-40 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-41 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-42 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-43 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-44 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-45 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-46 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-47 m/z = 826.25(C₅₈H₃₈N₂S₂ = 827.08) 1-48 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-49 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-50 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-51 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-52 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-53 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 1-54 m/z = 826.25(C₅₈H₃₈N₂S₂ = 827.08) 1-55 m/z = 806.19(C₅₄H₃₄N₂S₃ = 807.06) 1-56 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-57 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-58 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-59 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-60 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-61 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-62 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-63 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-64 m/z = 622.21(C₄₃H₃₀N₂OS = 622.79) 1-65 m/z = 688.20(C₄₇H₃₂N₂S₂ = 688.91) 1-66 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-67 m/z = 789.23(C₅₄H₃₅N₃S₂ = 790.02) 1-68 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-69 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-70 m/z = 642.16(C₄₂H₂₇FN₂S₂ = 642.81) 1-71 m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 1-72 m/z = 714.22(C₄₉H₃₄N₂S₂ = 714.95) 1-73 m/z = 716.20(C₄₈H₃₂N₂OS₂ = 716.92) 1-74 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 1-75 m/z = 634.24(C₄₅H₃₄N₂S = 634.84) 1-76 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 1-77 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-78 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-79 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-80 m/z = 748.22(C₅₂H₃₂N₂O₂S = 748.90) 1-81 m/z = 821.29(C₅₇H₃₅D₅N₂S₂ = 822.11) 1-82 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 1-83 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 1-84 m/z = 714.18(C₄₈H₃₀N₂OS₂ = 714.90) 1-85 m/z = 882.22(C₆₀H₃₈N₂S₃ = 883.16) 1-86 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-87 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-88 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-89 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-90 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-91 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 1-92 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-93 m/z = 688.20(C₄₇H₃₂N₂S₂ = 688.91) 1-94 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 1-95 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 1-96 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-97 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-98 m/z = 622.21(C₄₃H₃₀N₂OS = 622.79) 1-99 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 1-100 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 1-101 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 1-102 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 1-103 m/z = 628.25(C₄₆H₃₂N₂O = 628.78) 1-104 m/z = 693.28(C₅₀H₃₅N₃O = 693.85) 1-105 m/z = 723.23(C₅₀H₃₃N₃OS = 723.89) 1-106 m/z = 749.29(C₅₄H₃₁D₅N₂S = 749.99) 1-107 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-108 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-109 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-110 m/z = 724.25(C₅₁H₃₆N₂OS = 724.92) 1-111 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-112 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-113 m/z = 780.17(C₅₂H₃₂N₂S₃ = 781.02) 1-114 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-115 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 1-116 m/z = 698.20(C₄₈H₃₀N₂O₂S = 698.84) 1-117 m/z = 618.26(C₄₂H₁₈D₁₀N₂OS = 618.82) 1-118 m/z = 757.27(C₅₄H₃₅N₃O₂ = 757.89) 1-119 m/z = 668.25(C₄₈H₃₂N₂O₂ = 668.80) 1-120 m/z = 720.26(C₅₂H₃₆N₂S = 720.93) 1-121 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 1-122 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-123 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-124 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-125 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-126 m/z = 860.25(C₅₈H₄₀N₂O₂S₂ = 861.09) 1-127 m/z = 798.27(C₅₇H₃₈N₂OS = 799.00) 1-128 m/z = 734.33(C₅₄H₄₂N₂O = 734.94) 1-129 m/z = 742.26(C₅₄H₃₄N₂O₂ = 742.88) 1-130 m/z = 945.37(C₇₀H₄₇N₃O = 946.17) 1-131 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 1-132 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-133 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-134 m/z = 724.20(C₅₀H₃₂N₂S₂ = 724.94) 1-135 m/z = 816.26(C₅₇H₄₀N₂S₂ = 817.08) 1-136 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 1-137 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-138 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 1-139 m/z = 881.29(C₆₁H₄₃N₃S₂ = 882.16) 1-140 m/z = 704.28(C₅₂H₃₆N₂O = 704.87) 1-141 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 1-142 m/z = 682.23(C₄₈H₃₀N₂O₃ = 682.78) 1-143 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 1-144 m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.02) 1-145 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-146 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 1-147 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 1-148 m/z = 806.28(C₅₉H₃₈N₂S = 807.03) 1-149 m/z = 823.30(C₅₉H₃₈FN₃O = 823.97) 1-150 m/z = 743.29(C₅₄H₃₇N₃O = 743.91) 1-151 m/z = 998.33(C₇₃H₄₆N₂OS = 999.24) 1-152 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 1-153 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-154 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-155 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-156 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 1-157 m/z = 762.29(C₅₀H₄₆N₂SSi₂ = 763.16) 1-158 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 1-159 m/z = 784.25(C₅₆H₃₆N₂OS = 784.98) 1-160 m/z = 810.27(C₅₈H₃₈N₂OS = 811.02) 1-161 m/z = 860.29(C₆₂H₄₀N₂OS = 861.08) 1-162 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-163 m/z = 742.26(C₅₄H₃₄N₂O₂ = 742.88) 1-164 m/z = 828.26(C₅₈H₄₀N₂S₂ = 829.09) 1-165 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 1-166 m/z = 724.20(C₅₀H₃₂N₂S₂ = 724.94) 1-167 m/z = 834.27(C₆₀H₃₈N₂OS = 835.04) 1-168 m/z = 768.28(C₅₆H₃₆N₂O₂ = 768.92) 1-169 m/z = 830.19(C₅₆H₃₄N₂S₃ = 831.08) 1-170 m/z = 810.27(C₅₈H₃₈N₂OS = 811.02) 1-171 m/z = 810.31(C₅₉H₄₂N₂S = 811.06) 1-172 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 1-173 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 1-174 m/z = 783.27(C₅₆H₃₇N₃S = 783.99) 1-175 m/z = 808.25(C₅₈H₃₆N₂OS = 809.00)

Synthesis Example 2

The compound (final product) represented by Formula 2 according to the present invention may be prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 4 below, but is not limited thereto.

Synthesis Example of 1-1

After placing Sub 1(1) (34.7 g, 80 mmol) and Sub 2(1) (30.9 g, 80 mmol), K2CO3 (19.3 g, 140 mmol), Pd(PPh3)4 (2.8 g, 2.4 mmol) in a round bottom flask, THE and water were added to dissolve it, and then refluxed at 80° C. for 12 hours. When the reaction was completed, the temperature of the reaction product was cooled to room temperature, extracted with CH₂Cl₂, and washed with water. The organic layer was dried over MgSO₄, concentrated, and the resulting organic material was separated using a silicagel column to obtain the desired product (37.4 g, 71%).

Synthesis Example of 1-6

Sub 1(6) (44.6 g, 80 mmol) and Sub 2(2) (30.9 g, 80 mmol) were used to obtain a product (43.2 g, 69%) using the synthesis method of 1-1.

Synthesis Example of 1-12

Sub 1(12) (42.7 g, 80 mmol) and Sub 2(33) (34.9 g, 80 mmol) were used to obtain a product (42.7 g, 66%) using the synthesis method of 1-1.

Synthesis Example of 1-33

Sub 1(27) (40.8 g, 80 mmol) and Sub 2(9) (43.1 g, 80 mmol) were used to obtain a product (51.0 g, 72%) using the synthesis method of 1-1.

Synthesis Example of 1-44

Sub 1(27) (40.8 g, 80 mmol) and Sub 2(10) (37.0 g, 80 mmol) were used to obtain a product (45.4 g, 70%) using the synthesis method of 1-1.

Synthesis Example of 1-53

Sub 1(34) (44.0 g, 80 mmol) and Sub 2(29) (29.6 g, 80 mmol) were used to obtain a product (41.2 g, 68%) using the synthesis method of 1-1.

Synthesis Example of 1′-64

Sub 1(37) (48.2 g, 80 mmol) and Sub 2(34) (34.9 g, 80 mmol) were used to obtain a product (45.6 g, 71%) using the synthesis method of 1-1.

Synthesis Example of 1-75

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(35) (41.8 g, 80 mmol) were used to obtain a product (46.4 g, 73%) using the synthesis method of 1-1.

Synthesis Example of 2-1

Sub 1(1) (34.7 g, 80 mmol) and Sub 2(27) (37.0 g, 80 mmol) were used to obtain a product (42.3 g, 72%) using the synthesis method of 1-1.

Synthesis Example of 2-22

Sub 1(38) (50.7 g, 80 mmol) and Sub 2(24) (37.0 g, 80 mmol) were used to obtain a product (51.6 g, 69%) using the synthesis method of 1-1.

Synthesis Example of 2-33

Sub 1(27) (40.8 g, 80 mmol) and Sub 2(36) (49.2 g, 80 mmol) were used to obtain a product (53.9 g, 70%) using the synthesis method of 1-1.

Synthesis Example of 2-40

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(37) (43.1 g, 80 mmol) were used to obtain a product (44.7 g, 69%) using the synthesis method of 1-1.

Synthesis Example of 2-51

Sub 1(33) (36.0 g, 80 mmol) and Sub 2(38) (35.7 g, 80 mmol) were used to obtain a product (41.1 g, 70%) using the synthesis method of 1-1.

Synthesis Example of 2-55

Sub 1(39) (42.1 g, 80 mmol) and Sub 2(23) (37.0 g, 80 mmol) were used to obtain a product (44.9 g, 68%) using the synthesis method of 1-1.

Synthesis Example of 2-58

Sub 1(25) (34.7 g, 80 mmol) and Sub 2(39) (47.9 g, 80 mmol) were used to obtain a product (45.9 g, 66%) using the synthesis method of 1-1.

Synthesis Example of 3-10

Sub 1(37) (28.6 g, 80 mmol) and Sub 2(10) (37.0 g, 80 mmol) were used to obtain a product (38.9 g, 74%) using the synthesis method of 1-1.

Synthesis Example of P-41

Core 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.7 g, 41.3 mmol), THE and water were added in a round bottom flask and stirred at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 4.6 g of P-41. (Yield: 57%)

Synthesis Example of P-91

Core 1 (5 g, 14 mmol), Sub 9 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE and water were added in a round bottom flask and stirred at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 4.7 g of P-91. (Yield: 51%)

Synthesis Example of P-106

Core 1 (5 g, 14 mmol), Sub 16 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE and water were added in a round bottom flask and stirred at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 5.8 g of P-106. (Yield: 63%)

Synthesis Example of P-146

Core 1 (5 g, 14 mmol), Sub 2 (5.8 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE and water were added in a round bottom flask and stirred at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 4.7 g of P-146. (Yield: 51%)

Synthesis Example of P-4

Core 1 (5 g, 14 mmol), Sub 6 (5.9 g, 15.4 mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE and water were added in a round bottom flask and stirred at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 6.1 g of P-4. (Yield: 66%)

Synthesis Example of 4-1

Sub 1-1′ (50 g, 98.04 mmol) was added to a round bottom flask and dissolve with THE (359 mL), Sub 2-1′(52.51 g, 117.65 mmol), Pd(PPh3)4 (4.53 g, 3.92 mmol), K2CO3 (40.65 g, 294.12 mmol) and water (180 mL) were added and stirred to reflux. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. Thereafter, the concentrate was passed through a silicagel column and recrystallized to obtain 64.61 g of a product. (Yield: 83%)

Synthesis Example of 5-3

Sub 1-1″ (60 g, 133.35 mmol) was added to a round bottom flask and dissolve with THE (489 mL), Sub 2-3″(58.28 g, 160.01 mmol), Pd(PPh3)4 (6.16 g, 5.33 mmol), K2CO3 (55.29 g, 400.04 mmol), and water (244 mL) were added and stirred to reflux. When the reaction is complete, the resulting compound was extracted with ether and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 73.40 g of the product. (Yield: 75%)

Synthesis Example of 7-8

2-chloro-4-phenyl-6-(7-phenyldibenzo[b,d]furan-2-yl)-1,3,5-triazine (58 g, 133.35 mmol) was added to a round bottom flask and dissolve with THE (489 mL), [1,1′:3′,1″:3″,1″′-quaterphenyl]-3-ylboronic acid (56 g, 160.01 mmol), Pd(PPh₃)₄ (6.16 g, 5.33 mmol), K₂CO₃ (55.29 g, 400.04 mmol), and water (244 mL) were added and stirred to reflux. When the reaction is complete, the resulting compound was extracted with ether and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 71.33 g of the product. (Yield: 76%)

Synthesis Example of 7-20

2-chloro-4-phenyl-6-(8-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 46.1 mmol) was added in a round bottom flask and dissolved in THF (Tetrahydrofuran) (230 mL), and (8-([1,1′-biphenyl]-3-yl)dibenzo[b,d]furan-1-yl)boronic acid (16.8 g, 46.1 mmol), K₂CO₃ (19.1 g, 138 mmol), Pd(PPh₃)₄ (3.20 g, 2.77 mmol), water (115 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 25.1 g of the product. (Yield: 76%)

Synthesis Example of 8-1

2-chloro-4-phenyl-6-(8-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 46.1 mmol) was added in a round bottom flask and dissolved in THF (Tetrahydrofuran) (230 mL), and (8-phenyldibenzo[b,d]thiophen-1-yl)boronic acid (14.0 g, 46.1 mmol), K₂CO₃ (19.1 g, 138 mmol), Pd(PPh₃)₄ (3.20 g, 2.77 mmol), water (115 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 24.0 g of the product. (Yield: 79%)

Synthesis Example of 8-5

2-chloro-4-phenyl-6-(8-phenyldibenzo[b,d]furan-1-yl)-1,3,5-triazine (20.0 g, 46.1 mmol) was added in a round bottom flask and dissolved in THF (Tetrahydrofuran) (230 mL), and (9-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-3-yl)boronic acid (16.8 g, 46.1 mmol), K₂CO₃ (19.1 g, 138 mmol), Pd(PPh₃)₄ (3.20 g, 2.77 mmol), water (115 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 24.2 g of the product. (Yield: 73%)

Synthesis Example of 8-13

(1) Synthesis Example of Sub1(A)-1

1-bromo-7-chlorodibenzo[b,d]furan (25.0 g, 88.8 mmol) was added in a round bottom flask and dissolved in THF (Tetrahydrofuran) (444 mL), and (9,9-dimethyl-9H-fluoren-3-yl)boronic acid (21.1 g, 88.8 mmol), K₂CO₃ (36.8 g, 266 mmol), Pd(PPh₃)₄ (6.16 g, 5.33 mmol), water (222 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 26.7 g of the product. (Yield: 76%)

(2) Synthesis Example of Sub1(A)

The obtained Sub(A)-1 (26.7 g, 67.5 mmol) was dissolved in DMF (Dimethylformamide) (337 mL), and bis(pinacolato)diboron (18.9 g, 74.2 mmol), KOAc (19.9 g, 203 mmol), PdCl₂(dppf) (1.48 g, 2.02 mmol) were added and stirred at 120° C. After the reaction was completed, DMF was removed through distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 23.6 g of the product. (Yield: 72%)

(3) Synthesis Example of 8-13

2-chloro-4-phenyl-6-(8-phenyldibenzo[b,d]thiophen-1-yl)-1,3,5-triazine (20.0 g, 44.4 mmol) was added in a round bottom flask and dissolved in THE (222 mL), and Sub1(A) (21.6 g, 44.4 mmol), K₂CO₃ (18.4 g, 133 mmol), Pd(PPh₃)₄ (3.08 g, 2.67 mmol), water (111 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 25.8 g of the product. (Yield: 75%)

Synthesis Example of 8-27

2-chloro-4-phenyl-6-(7-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine (20.0 g, 46.1 mmol) was added in a round bottom flask and dissolved in THE (222 mL), and (8-([1,1′-biphenyl]-3-yl)dibenzo[b,d]furan-1-yl)boronic acid (16.8 g, 46.1 mmol), K₂CO₃ (19.1 g, 138 mmol), Pd(PPh₃)₄ (3.20 g, 2.77 mmol), water (115 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 25.8 g of the product. (Yield: 78%)

TABLE 4 compound FD-MS 1′-1 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1′-2 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-3 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-4 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1′-5 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1′-6 m/z = 781.22(C₅₅H₃₁N₃OS = 781.93) 1′-7 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-8 m/z = 721.22(C₅₀H₃₁N₃OS = 721.88) 1′-9 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-10 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-11 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-12 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1′-13 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-14 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-15 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-16 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05) 1′-17 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1′-18 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1′-19 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1′-20 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05) 1′-21 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-22 m/z = 857.25(C₆₁H₃₅N₃OS = 858.03) 1′-23 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 1′-24 m/z = 825.23(C₅₇H₃₂FN₃OS = 825.96) 1′-25 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1′-26 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-27 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-28 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-29 m/z = 732.22(C₅₁H₃₁N₃OS = 733.89) 1′-30 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-31 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1′-32 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-33 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 1′-34 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-35 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-36 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-37 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-38 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-39 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-40 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1′-41 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1′-42 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-43 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-44 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-45 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-46 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-47 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 1′-48 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1′-49 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1′-50 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-51 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-52 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1′-53 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1′-54 m/z = 781.22(C₅₅H₃₁N₃OS = 781.93) 1′-55 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 1′-56 m/z = 721.22(C₅₀H₃₁N₃OS = 721.88) 1′-57 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-58 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 1′-59 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1′-60 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1′-61 m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91) 1′-62 m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91) 1′-63 m/z = 749.20(C₅₁H₃₁N₃S₂ = 749.95) 1′-64 m/z = 875.24(C₆₁H₃₇N₃S₂ = 876.11) 1′-65 m/z = 823.21(C₅₇H₃₃N₃S₂ = 824.03) 1′-66 m/z = 773.20(C₅₃H₃₁N₃S₂ = 773.97) 1′-67 m/z = 799.21(C₅₅H₃₃N₃S₂ = 800.01) 1′-68 m/z = 875.24(C₆₁H₃₇N₃S₂ = 876.11) 1′-69 m/z = 749.20(C₅₁H₃₁N₃S₂ = 749.95) 1′-70 m/z = 873.23(C₆₁H₃₅N₃S₂ = 874.09) 1′-71 m/z = 849.23(C₅₉H₃₅N₃S₂ = 850.07) 1′-72 m/z = 791.19(C₅₃H₃₀FN₃S₂ = 791.96) 1′-73 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 1′-74 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1′-75 m/z = 798.30(C₅₇H₃₀D₅N₃O₂ = 799.0) 1′-76 m/z = 843.29(C₆₁H₃₇N₃O₂ = 843.99) 1′-77 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1′-78 m/z = 717.24(C₅₁H₃₁N₃O₃ = 717.83) 1′-79 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 1′-80 m/z = 793.27(C₅₇H₃₅N₃O₂ = 793.93) 1′-81 m/z = 869.30(C₆₃H₃₉N₃O₂ = 870.02) 1′-82 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 1′-83 m/z = 722.27(C₅₁H₂₆D₅N₃O₂ = 722.9) 1′-84 m/z = 793.27(C₅₇H₃₅N₃O₂ = 793.93) 2-1 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 2-2 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-3 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-4 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05) 2-5 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 2-6 m/z = 857.25(C₆₁H₃₅N₃OS = 858.03) 2-7 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-8 m/z = 797.25(C₅₆H₃₅N₃OS = 797.98) 2-9 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-10 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-11 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-12 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 2-13 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-14 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 2-15 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-16 m/z = 935.30(C₆₇H₄₁N₃OS = 936.15) 2-17 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) 2-18 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) 2-19 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-20 m/z = 909.28(C₆₅H₃₉N₃OS = 910.11) 2-21 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-22 m/z = 933.28(C₆₇H₃₉N₃OS = 934.13) 2-23 m/z = 909.28(C₆₅H₃₉N₃OS = 910.11) 2-24 m/z = 851.24(C₅₉H₃₄FN₃OS = 852.00) 2-25 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 2-26 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-27 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-28 m/z = 935.30(C₆₇H₄₁N₃OS = 936.15) 2-29 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-30 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-31 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 2-32 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-33 m/z = 961.31(C₆₉H₄₃N₃OS = 962.18) 2-34 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-35 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-36 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-37 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-38 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-39 m/z = 961.31(C₆₉H₄₃N₃OS = 962.18) 2-40 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-41 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-42 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-43 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-44 m/z = 1032.40(C₇₄H₅₄N₃OS = 1033.33) 2-45 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-46 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-47 m/z = 961.31(C₆₉H₄₃N₃OS = 962.18) 2-48 m/z = 859.27(C₆₁H₃₇N₃OS = 860.08) 2-49 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-50 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 2-51 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 2-52 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 2-53 m/z = 977.29(C₆₉H₄₃N₃S₂ = 978.24) 2-54 m/z = 825.23(C₅₇H₃₅N₃S₂ = 826.05) 2-55 m/z = 825.23(C₅₇H₃₅N₃S₂ = 826.05) 2-56 m/z = 901.26(C₆₃H₃₉N₃S₂ = 902.15) 2-57 m/z = 869.30(C₆₃H₃₉N₃O₂ = 870.02) 2-58 m/z = 869.30(C₆₃H₃₉N₃O₂ = 870.02) 2-59 m/z = 945.34(C₆₉H₄₃N₃O₂ = 946.12) 2-60 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-1 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-2 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-3 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-4 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 3-5 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 3-6 m/z = 731.20(C₅₁H₂₉N₃OS = 731.87) 3-7 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-8 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-9 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-10 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-11 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-12 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 3-13 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 3-14 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-15 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 3-16 m/z = 799.21(C₅₅H₃₃N₃S₂ = 800.01) 3-17 m/z = 647.15(C₄₃H₂₅N₃S₂ = 647.81) 3-18 m/z = 747.18(C₅₁H₂₉N₃S₂ = 747.93) 3-19 m/z = 565.18(C₃₉H₂₃N₃O₂ = 565.63) 3-20 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 3-21 m/z = 722.27(C₅₁H₂₆D₅N₃S₂ = 722.86) 3-22 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-23 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-24 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 3-25 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 3-26 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 3-27 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) 3-28 m/z = 859.27(C₆₁H₃₇N₃OS = 860.05) 3-29 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 3-30 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 3-31 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-32 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-33 m/z = 885.28(C₆₃H₃₉N₃OS = 886.09) 3-34 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) 3-35 m/z = 673.16(C₄₅H₂₇N₃S₂ = 673.85) 3-36 m/z = 793.27(C₅₇H₃₅N₃O₂ = 793.93) P-1 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) P-2 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-3 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-4 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-5 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-6 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-7 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-8 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-9 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-10 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-11 m/z = 586.19(C₃₉H₁₈D₅N₃OS = 586.7) P-12 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-13 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-14 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-15 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-16 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-17 m/z = 636.20(C₄₃H₂₀D₅N₃OS = 636.8) P-18 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-19 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-20 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-21 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-22 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-23 m/z = 636.20(C₄₃H₂₀D₅N₃OS = 636.8) P-24 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-25 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-26 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-27 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-28 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-29 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.8) P-30 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) P-31 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) P-32 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-33 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-34 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-35 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-36 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-37 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-38 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-39 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-40 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-41 m/z = 586.19(C₃₉H₁₈D₅N₃OS = 586.7) P-42 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-43 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-44 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-45 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-46 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-47 m/z = 636.20(C₄₃H₂₀D₅N₃OS = 636.8) P-48 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-49 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-50 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-51 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-52 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-53 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-54 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-55 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-56 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-57 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-58 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-59 m/z = 662.22(C₄₅H₂₂DN₃OS = 662.82) P-60 m/z = 662.22(C₄₅H₂₂DN₃OS = 662.82) P-61 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-62 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-63 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-64 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-65 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-66 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-67 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-68 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-69 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-70 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-71 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.8) P-72 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-73 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-74 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-75 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-76 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-77 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-78 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-79 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-80 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-81 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-82 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-83 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-84 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-85 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-86 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-87 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-88 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-89 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-90 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-91 m/z = 662.22(C₄₅H₂₂DN₃OS = 662.82) P-92 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-93 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-94 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-95 m/z = 762.25(C₅₃H₂₆D₅N₃OS = 762.9) P-96 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-97 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-98 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-99 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-100 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-101 m/z = 667.2(C₄₅H₁₇D₁₀N₃OS = 667.9) P-102 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-103 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-104 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-105 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-106 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-107 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-108 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-109 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-110 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-111 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-112 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-113 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-114 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-115 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-116 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) P-117 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-118 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-119 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-120 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-121 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-122 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-123 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-124 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-125 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-126 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-127 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-128 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-129 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-130 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-131 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-132 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-133 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-134 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-135 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-136 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) P-137 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-138 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-139 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-140 m/z = 762.25(C₅₃H₂₆D₅N₃OS = 762.94) P-141 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.9) P-142 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-143 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-144 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-145 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.9) P-146 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-147 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-148 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) P-149 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-150 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) P-151 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-152 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-153 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.8) p-154 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) p-155 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-156 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-157 m/z = 681.19(C₄₅H₂₇N₃OS = 681.81) p-158 m/z = 681.19(C₄₅H₂₇N₃OS = 681.81) P-159 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) p-160 m/z = 781.22(C₅₅H₃₁N₃OS = 781.93) 4-1 m/z = 793.27 (C₅₇H₃₅N₃O₂ = 793.93) 4-2 m/z = 869.30 (C₆₃H₃₉N₃O₂ = 870.02) 4-4 m/z = 798.3(C₅₇H₃₀D₅N₃O₂ = 798.96) 4-7 m/z = 919.32 (C₆₇H₄₁N₃O₂ = 920.08) 4-8 m/z = 843.29 (C₆₁H₃₇N₃O₂ = 843.99) 4-10 m/z = 945.34 (C₆₉H₄₃N₃O₂ = 946.12) 4-11 m/z = 944.32 (C₆₈H₄₀N₄O₂ = 945.09) 4-12 m/z = 970.33 (C₇₀H₄₂N₄O₂ = 971.13) 5-1 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) 5-2 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) 5-3 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) 5-4 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) 5-7 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) 5-8 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) 5-9 m/z = 859.27 (C₆₁H₃₇N₃OS = 860.05) 5-10 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) 5-11 m/z = 808.23 (C₅₆H₃₂N₄OS = 808.96) 5-12 m/z = 890.31 (C₆₃H₃₄D₅N₃OS = 891.1) 5-13 m/z = 824.24 (C₅₅H₃₂N₆OS = 824.96) 5-14 m/z = 752.20 (C₅₀H₂₉FN₄OS = 752.87) 5-15 m/z = 765.26 (C₅₁H₃₅N₅OS = 765.94) 5-16 m/z = 765.17 (C₄₉H₂₇N₅OS₂ = 765.91) 5-17 m/z = 807.23 (C₅₇H₃₃N₃OS = 807.97) 5-18 m/z = 833.25 (C₅₉H₃₅N₃OS = 834.01) 5-19 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) 5-20 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) 7-1 m/z = 627.23(C₄₅H₂₉N₃O = 627.75) 7-2 m/z = 627.23(C₄₅H₂₉N₃O = 627.75) 7-3 m/z = 643.21(C₄₅H₂₉N₃S = 643.81) 7-4 m/z = 703.26(C₅₁H₃₃N₃O = 703.85) 7-5 m/z = 627.23(C₄₅H₂₉N₃O = 627.75) 7-6 m/z = 627.23(C₄₅H₂₉N₃O = 627.75) 7-7 m/z = 703.26(C₅₁H₃₃N₃O = 703.85) 7-8 m/z = 703.26(C₅₁H₃₃N₃O = 703.85) 7-9 m/z = 627.23(C₄₅H₂₉N₃O = 627.75) 7-10 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 7-11 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 7-12 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 7-13 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-14 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-15 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-16 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 7-17 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 7-18 m/z = 581.16(C₃₉H₂₃N₃OS = 581.69) 7-19 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-20 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 7-21 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 7-22 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-23 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 7-24 m/z = 641.21(C₄₅H₂₇N₃O₂ = 641.73) 8-1 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 8-2 m/z = 749.2(C₅₁H₃₁N₃S₂ = 749.95) 8-3 m/z = 717.24(C₅₁H 

 N₃O₂ = 717.83) 8-4 m/z = 658.18(C₄₄H₂₆N₄OS = 658.78) 8-5 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 8-6 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 8-7 m/z = 823.23(C₅₇H₃₃N₃O₂S = 823.97) 8-8 m/z = 762.19(C₅₁H₃₀N₄S₂ = 762.95) 8-9 m/z = 914.25(C₆₃H₃₈N₄S₂ = 915.15) 8-10 m/z = 747.2(C₅₁H₂₉N₃O₂S = 747.87) 8-11 m/z = 849.28(C₆₀H₃₉N₃OS = 850.05) 8-12 m/z = 734.21(C₅₀H₃₀N₄OS = 734.88) 8-13 m/z = 773.25(C₅₄H₃₅N₃OS = 773.95) 8-14 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 8-15 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 8-16 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 8-17 m/z = 666.21(C₄₆H₂₆N₄O₂ = 666.74) 8-18 m/z = 729.23(C₄₉H₃₅N₃S₂ = 729.96) 8-19 m/z = 774.21(C₅₂H₃₀N₄O₂S = 774.9) 8-20 m/z = 747.2(C₅₁H₂₉N₃O₂S = 747.87) 8-21 m/z = 697.27(C₄₉H₃₅N₃O₂ = 697.84) 8-22 m/z = 659.2(C₄₅H₂₆FN₃O₂ = 659.72) 8-23 m/z = 839.21(C₅₇H₃₃N₃OS₂ = 840.03) 8-24 m/z = 682.18(C₄₆H₂₆N₄OS = 682.8) 8-25 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 8-26 m/z = 749.2(C₅₁H₃₁N₃S₂ = 749.95) 8-27 m/z = 717.24(C₅₁H₃₁N₃O₂ = 717.83) 8-28 m/z = 767.26(C₅₅H₃₃N₃O₂ = 767.89) 8-29 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 8-30 m/z = 666.21(C₄₆H₂₆N₄O₂ = 666.74) 8-31 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) 8-32 m/z = 675.18(C₄₅H₂₆FN₃OS = 675.78) 8-33 m/z = 646.24(C₄₅H₂₂D₅N₃O₂ = 646.76) 8-34 m/z = 646.24(C₄₅H₂₂D₅N₃O₂ = 646.76) 8-35 m/z = 749.20(C₅₁H₃₁N₃S₂ = 749.95) 8-36 m/z = 662.22(C₄₅H₂₂D₅N₃OS = 662.82) 8-37 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 8-38 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89)

Synthesis Example 3

The compound represented by Formula 26 according to the present invention (final product 3) is synthesized as shown in Scheme 5 below, but is not limited thereto.

Synthesis Example of 9-1

After dissolving 9-phenyl-9H,9′H-3,3′-bicarbazole (20.0 g, 49.0 mmol) in a round bottom flask with toluene (245 mL), and 3-chloro-7-phenyldibenzo[b,d]furan (13.6 g, 49.0 mmol), Pd₂(dba)₃ (1.34 g, 1.47 mmol), P(t-Bu)₃ (0.59 g, 2.94 mmol), NaOt-Bu (9.4 g, 97.9 mmol) was added and refluxed. When the reaction was completed, the product was extracted with CH₂Cl₂ and water, and the organic layer was dried over MgSO₄ and concentrated, and the resulting compound was recrystallized with a silicagel column to obtain 23.3 g (yield 73%) of the product.

Synthesis Example of 9-3

After dissolving 9-phenyl-9H,9′H-3,3′-bicarbazole (20.0 g, 49.0 mmol) in a round bottom flask with toluene (245 mL), 7-chloro-2-phenyldibenzo[b,d]furan (13.6 g, 1.47 mmol), Pd₂(dba)3 (1.34 g, 1.47 mmol), P(t-Bu)3 (0.59 g, 2.94 mmol), NaOt-Bu (9.4 g, 97.9 mmol) was added and refluxed. When the reaction was completed, the product was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and the resulting compound was recrystallized in a silicagel column to obtain 22.6 g (yield 71%) of the product.

Synthesis Example of 9-10

After dissolving 6,9-diphenyl-9H,9′H-3,3′-bicarbazole (20.0 g, 41.3 mmol) in a round bottom flask with toluene (206 mL), 8-chloro-1-phenyldibenzo[b,d]furan (11.5 g, 41.3 mmol), Pd₂(dba)₃ (1.13 g, 1.24 mmol), P(t-Bu)₃ (0.50 g, 2.48 mmol), NaOt-Bu (7.9 g, 82.5 mmol) were added and refluxed. When the reaction was completed, the product was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and the resulting compound was recrystallized in a silicagel column to obtain 19.8 g (yield 66%) of the product.

Synthesis Example of 9-15

After dissolving N,N,9-triphenyl-9H,9′H-[3,3′-bicarbazol]-6-amine (20.0 g, 34.7 mmol) in a round bottom flask with toluene (174 mL), 3-chloro-6-phenyldibenzo[b,d]furan (9.7 g, 34.7 mmol), Pd₂(dba)₃ (0.95 g, 1.04 mmol), P(t-Bu)₃ (0.42 g, 2.08 mmol), NaOt-Bu (6.7 g, 69.5 mmol) were added and refluxed. When the reaction was completed, the product was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and the resulting compound was recrystallized in a silicagel column to obtain 21.3 g (yield 75%) of the product.

Synthesis Example of 9-32

After dissolving 9-(dibenzo[b,d]furan-3-yl)-9H,9′H-3,3′-bicarbazole (20.0 g, 40.1 mmol) in a round bottom flask with toluene (201 mL), 2-chloro-6-phenyldibenzo[b,d]thiophene (11.8 g, 40.1 mmol), Pd₂(dba)₃ (1.10 g, 1.20 mmol), P(t-Bu)₃ (0.49 g, 2.41 mmol), NaOt-Bu (7.7 g, 80.2 mmol) were added and refluxed. When the reaction was completed, the product was extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated, and the resulting compound was recrystallized in a silicagel column to obtain 21.9 g (yield 72%) of the product.

TABLE 5 compound FD-MS 9-1 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 9-2 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-3 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 9-4 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-5 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-6 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 9-7 m/z = 756.22(C₅₄H₃₂N₂OS = 756.92) 9-8 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 9-9 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 9-10 m/z = 726.27(C₅₄H₃₄N₂O = 726.88) 9-11 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-12 m/z = 700.25(C₅₂H₃₂N₂O = 700.84) 9-13 m/z = 653.22(C₄₅H₂₇N₅O = 653.75) 9-14 m/z = 756.22(C₅₄H₃₂N₂OS = 756.92) 9-15 m/z = 817.31(C₆₀H₃₉N₃O = 817.99) 9-16 m/z = 792.26(C₅₈H₃₆N₂S = 793) 9-17 m/z = 716.23(C₅₂H₃₂N₂S = 716.9) 9-18 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-19 m/z = 742.24(C₅₄H₃₄N₂S = 742.94) 9-20 m/z = 726.27(C₅₄H₃₄N₂O = 726.88) 9-21 m/z = 766.3(C₅₇H₃₈N₂O = 766.94) 9-22 m/z = 868.29(C₆₄H₄₀N₂S = 869.1) 9-23 m/z = 766.3(C₅₇H₃₈N₂O = 766.94) 9-24 m/z = 920.29(C₆₇H₄₀N₂OS = 921.13) 9-25 m/z = 888.31(C₆₇H₄₀N₂O = 889.07) 9-26 m/z = 700.25(C₅₂H₃₂N₂O = 700.84) 9-27 m/z = 826.3(C₆₂H₃₈N₂O = 827) 9-28 m/z = 818.28(C₆₀H₃₈N₂S = 819.04) 9-29 m/z = 816.26(C₆₀H₃₆N₂S = 817.02) 9-30 m/z = 802.3(C₆₀H₃₈N₂O = 802.98) 9-31 m/z = 995.33(C₇₃H₄₅N₃S = 996.24) 9-32 m/z = 756.22(C₅₄H₃₂N₂OS = 756.92) 9-33 m/z = 655.27(C₄₈H₂₅D₅N₂O = 655.81) 9-34 m/z = 655.27(C₄₈H₂₅D₅N₂O = 655.81) 9-35 m/z = 726.27(C₅₄H₃₄N₂O = 726.88) 9-36 m/z = 696.40(C₄₈D₃₀N₂S = 697.03)

Evaluation of Manufacture of Organic Electric Element Example 1) Manufacture and Evaluation of Green Organic Light Emitting Diode

First, on an ITO layer(anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenyl benzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited to form a hole transport layer with a thickness of 60 nm. Subsequently, as a host, a mixture of the compounds of the present invention represented by Formula 1 and Formula 2 at 6:4 was used, and a dopant, by doping Ir(ppy)₃ [tris(2-phenylpyridine)-iridium]at 95:5 weight, an emitting layer having a thickness of 30 nm was deposited on the hole transport layer. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 1

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 1 was used as a host alone.

Comparative Examples 2

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 2 was used as a host alone.

Comparative Examples 3

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 3 was used as a host alone.

Comparative Examples 4, Comparative Examples 5

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula 2 was used as a host alone.

Comparative Examples 6

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compound 1 and the compound represented by Formula 2 were mixed and used as a host.

Comparative Examples 7

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compound 2 and the compound represented by Formula 2 were mixed and used as a host.

Comparative Examples 8

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compound 3 and the compound represented by Formula 2 were mixed and used as a host.

TABLE 6 Current Brightness Lifetime First host Second host Voltage Density (cd/m2) Efficiency T(95) comparative comparative — 5.5 19.5 5000.0 25.6 80.4 example(1) compound 1 comparative comparative — 5.9 46.3 5000.0 10.8 20.3 example (2) compound 2 comparative comparative — 6.0 48.5 5000.0 10.3 23.8 example (3) compound 3 comparative — compound 1′-25 5.3 15.7 5000.0 31.9 60.8 example (4) comparative — compound P-26 5.1 14.8 5000.0 33.8 58.2 example (5) comparative comparative compound P-26 4.8 12.3 5000.0 40.8 129.9 example (6) compound 1 comparative comparative compound P-26 4.6 13.6 5000.0 36.9 70.4 example (7) compound 2 comparative comparative compound P-26 4.5 12.9 5000.0 38.7 75.6 example (8) compound 3 example(1) compound 1-2 compound 1′-25 4.1 11.7 5000.0 42.8 130.3 example(2) compound P-8 4.3 11.2 5000.0 44.5 130.1 example(3) compound P-26 4.3 11.6 5000.0 43.2 131.0 example(4) compound P-69 4.1 11.3 5000.0 44.3 130.9 example(5) compound 4-5 4.1 11.5 5000.0 43.6 132.5 example(6) compound 5-2 4.1 11.3 5000.0 44.2 132.9 example(7) compound 6-4 4.2 11.5 5000.0 43.3 131.5 example(8) compound 1-16 compound 1′-25 4.2 11.6 5000.0 43.2 132.5 example(9) compound P-8 4.0 12.1 5000.0 41.5 132.8 example(10) compound P-26 4.0 12.1 5000.0 41.2 131.8 example(11) compound P-69 4.1 12.5 5000.0 40.1 131.3 example(12) compound 4-5 4.3 11.9 5000.0 42.0 130.2 example(13) compound 5-2 4.2 11.2 5000.0 44.8 130.7 example(14) compound 6-4 4.1 11.3 5000.0 44.2 130.7 example(15) compound 1-36 compound 1′-25 3.7 10.3 5000.0 48.4 136.8 example(16) compound P-8 3.8 10.2 5000.0 48.8 136.1 example(17) compound P-26 3.8 10.3 5000.0 48.6 137.5 example(18) compound P-69 3.8 10.1 5000.0 49.5 139.0 example(19) compound 4-5 3.8 10.1 5000.0 49.3 136.2 example(20) compound 5-2 3.9 11.0 5000.0 45.3 139.9 example(21) compound 6-4 3.8 10.5 5000.0 47.7 136.0 example(22) compound 1-64 compound 1′-25 3.8 10.5 5000.0 47.7 136.5 example(23) compound P-8 3.8 10.1 5000.0 49.7 135.5 example(24) compound P-26 3.8 10.3 5000.0 48.4 136.4 example(25) compound P-69 3.8 10.4 5000.0 47.9 137.6 example(26) compound 4-5 3.8 10.6 5000.0 47.3 139.5 example(27) compound 5-2 3.7 10.1 5000.0 49.6 136.1 example(28) compound 6-4 3.9 10.2 5000.0 48.8 139.8 example(29) compound 1-74 compound 1′-25 4.2 10.4 5000.0 48.1 138.7 example(30) compound P-8 4.1 10.1 5000.0 49.7 135.4 example(31) compound P-26 4.2 10.6 5000.0 47.3 136.6 example(32) compound P-69 4.0 10.2 5000.0 49.0 136.8 example(33) compound 4-5 4.1 10.7 5000.0 46.7 138.5 example(34) compound 5-2 4.2 10.2 5000.0 48.9 135.1 example(35) compound 6-4 4.3 10.7 5000.0 46.7 139.6 example(36) compound compound 1′-25 3.8 10.2 5000.0 49.2 137.4 example(37) 1-100 compound P-8 3.8 10.1 5000.0 49.5 139.8 example(38) compound P-26 3.9 10.2 5000.0 49.2 138.4 example(39) compound P-69 3.8 10.9 5000.0 46.1 140.0 example(40) compound 4-5 3.7 10.7 5000.0 46.9 135.4 example(41) compound 5-2 3.8 10.9 5000.0 45.8 138.4 example(42) compound 6-4 3.7 10.5 5000.0 47.5 138.3 example(43) compound compound 1′-25 3.8 12.5 5000.0 40.0 130.6 example(44) 1-122 compound P-8 3.8 11.5 5000.0 43.5 131.9 example(45) compound P-26 3.9 11.6 5000.0 43.1 131.5 example(46) compound P-69 3.7 12.0 5000.0 41.6 132.9 example(47) compound 4-5 3.7 11.3 5000.0 44.2 132.3 example(48) compound 5-2 3.8 11.2 5000.0 44.6 130.6 example(49) compound 6-4 3.8 11.7 5000.0 42.9 131.4 example(50) compound compound 1′-25 4.3 11.8 5000.0 42.5 130.7 example(51) 1-141 compound P-8 4.1 12.5 5000.0 40.1 132.2 example(52) compound P-26 4.2 11.2 5000.0 44.7 132.7 example(53) compound P-69 4.2 11.3 5000.0 44.3 132.9 example(54) compound 4-5 4.3 11.6 5000.0 42.9 130.7 example(55) compound 5-2 4.1 11.4 5000.0 44.0 130.6 example(56) compound 6-4 4.2 12.1 5000.0 41.3 131.7

As can be seen from the results of Table 5, when the material for an organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 is mixed and used as a phosphorescent host (Examples 1 to 56), compared to devices using a single compound (Comparative Examples 1 to 5) or devices mixed with a comparative compound (Comparative Examples 6 to 8), the driving voltage, efficiency, and lifespan are significantly improved. When the tertiary amine compounds, Comparative Compound 2 and Comparative Compound 3, were used as a phosphorescent host as a single material, both driving, efficiency and lifespan showed poor results, and Comparative compound 1 was the best in lifespan. When the compound represented by Formula 2 was used alone, there was a slight increase in driving and efficiency compared to the comparative compounds, but when Comparative Compounds 1 to 3 and the compound represented by Formula 2 were mixed and used as a phosphorescent host, all effects were improved compared to when used as a single compound. When Comparative Compound 1 with strong hole transport ability and the compound represented by Formula 2 were mixed, it showed a remarkable effect in terms of lifespan, and when the tertiary amine compounds, Comparative Compound 2 and Comparative Compound 3 were mixed, a remarkable effect was exhibited in terms of driving. From this result alone, it can be seen that even a compound with poor performance with a single host can improve the effect when mixed with a compound with a good charge balance.

In addition, it was confirmed that Examples 1 to 56 in which the compounds of Formula 1 and Formula 2 of the present invention were mixed and used as a host were significantly improved than in the case of Comparative Examples 1 to 8.

Based on the above experimental results, the present inventors determined that in the case of a mixture of the compound of Formula 1 and the compound of Formula 2, each of the compounds has novel properties other than those of the compound, and measured the PL lifetime using the compound of Formula 1, the compound of Formula 2, and the mixture of the present invention, respectively. As a result, it was confirmed that when the compounds of the present invention, Formula 1 and Formula 2, were mixed, a new PL wavelength was formed unlike the single compound, and the decrease and disappearance time of the newly formed PL wavelength increased from about 60 times to about 360 times less than the decrease and disappearance time of each of the compounds of Formula 1 and Formula 2. It is considered when mixed with the compound of the present invention, not only electrons and holes are moved through the energy level of each compound, but also the efficiency and life span are increased by electron, hole transport or energy transfer by a new region(exciplex) having a new energy level formed due to mixing. As a result, when the mixture of the present invention is used, the mixed thin film is an important example showing exciplex energy transfer and light emitting process.

Also, the reason why the combination of the present invention is superior to Comparative Examples 6 to 8 in which a comparative compound is mixed and used as a phosphorescent host is that the hole characteristics are improved by using a compound represented by Formula 1 in which one more amine group is added in Comparative Compounds 2 and 3, and has a good electrochemical synergy effect with the compound represented by Formula 2, which has strong electron properties. Accordingly, the charge balance between holes and electrons in the emission layer is increased, so that light emission is well performed inside the emitting layer rather than the hole transport layer interface, thereby reducing deterioration at the HTL interface, maximizing the driving voltage, efficiency, and lifespan of the entire device.

Example 2) Manufacture and Evaluation of Green Organic Light Emitting Diode by Mixing Ratio

TABLE 7 Mixing ratio First Second (first host:sec- Current Brightness Lifetime host host ond host) Voltage Density (cd/m2) Efficiency T(95) example(57) compound compound 7:3 3.9 10.2 5000.0 49.1 140.2 example(58) 1-36 1′-25 5:5 3.8 10.7 5000.0 46.8 130.3 example(59) 4:6 3.6 11.1 5000.0 45.2 125.7 example(60) 3:7 3.8 11.2 5000.0 44.6 120.6 example(61) compound compound 7:3 4.0 10.0 5000.0 50.1 139.4 example(62) 1-64 P-26 5:5 3.7 10.9 5000.0 45.8 130.5 example(63) 4:6 3.6 11.5 5000.0 43.5 123.4 example(64) 3:7 3.8 12.3 5000.0 40.7 120.2

As shown in Table 6, a device was manufactured and measured in the same manner as in Example 1 by using a mixture of the compounds of the present invention in different ratios (7:3, 5:5, 4:6, 3:7). As a result of measuring by ratio, in the case of 7:3, it was similar to the result of Example 1, which was measured as 6:4, but in the case of 5:5, 4:6, and 3:7 where the ratio of the first host decreases, the results of driving voltage, efficiency, and lifespan gradually declined. This can be explained because when an appropriate amount of the compound represented by Formula 1 having strong hole properties such as 7:3 and 4:6 is mixed, the charge balance in the emitting layer is maximized.

Example 3) Manufacture and Evaluation of Green Organic Light Emitting Diode

First, on an ITO layer(anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) was vacuum-deposited on the film to form a hole transport layer with a thickness of 60 nm. Subsequently, as a host, the compounds of the present invention represented by Formula 19 and Formula 21 was used, and as a dopant, by doping Ir(ppy)₃ [tris(2-phenylpyridine)-iridium] at 5:5 weight, an emitting layer having a thickness of 30 nm was deposited on the hole transport layer. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 9-12

An organic electroluminescent device was manufactured in the same manner as in Example 3, except that Comparative Compounds 4 to 7 were used as a single host, respectively.

TABLE 8 Current Brightness Efficiency CIE compound Voltage Density (cd/m²) (cd/A) T(95) x y comparative comparative 5.5 17.6 5000.0 28.4 74.2 0.30 0.63 example(9) compound 4 comparative comparative 5.9 14.4 5000.0 34.7 65.4 0.34 0.65 example(10) compound 5 comparative comparative 6.2 11.4 5000.0 43.8 80.6 0.33 0.60 example(11) compound 6 comparative comparative 6.6 11.3 5000.0 44.1 84.3 0.33 0.62 example(12) compound 7 example(65) compound(7-1) 5.2 9.3 5000.0 53.8 100.5 0.32 0.61 example(66) compound(7-7) 5.2 9.6 5000.0 52.0 104.8 0.31 0.62 example (67) compound(7-10) 5.1 9.3 5000.0 53.8 100.7 0.35 0.62 example(68) compound(7-13) 4.9 8.8 5000.0 56.7 104.7 0.31 0.63 example(69) compound(7-19) 5.2 9.1 5000.0 54.7 103.0 0.30 0.63 example(70) compound(7-21) 5.1 9.3 5000.0 53.6 102.0 0.30 0.61

As described above, it can be seen that the organic electroluminescent device using the compound of the present invention as a phosphorescent host significantly improves all of the driving voltage, efficiency, and lifespan compared to the organic electroluminescent device using the comparative compound. The difference between Comparative Compound 4 and the present invention is the difference in the presence or absence of a linking group of m-phenylene, and Comparative Compound 5 and Comparative Compound 6 differ in the presence or absence of secondary substituents such as phenyl and biphenyl in dibenzofuran, and Comparative compound 7 differs according to the number of substitutions of dibenzofuran. Comprehensively judging the device data, it was confirmed that the linker of m-phenylene has an effect of improving the efficiency, and the secondary substituent of dibenzouran has the effect of remarkably improving the lifespan, in particular. This means that even with the same core, the energy level of the compound (HOMO level, LUMO level, T1 level) is significantly different as a specific substituent is substituted, this difference in physical properties of the compound acts as a major factor (for example, energy balance) to improve device performance during device deposition, suggesting that these different device results may be derived.

Example 4) Green Organic Light Emitting Diode

The compound of the present invention was used as a green host material to fabricate an organic electric element according to a conventional method. First, on an ITO layer(anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) film was vacuum deposited to form a hole injection layer with a thickness of 60 nm. Then on the film 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) was vacuum deposited to form a hole transport layer with a thickness of 60 nm. Subsequently, a mixture in which the compound represented by Formula 25 and the compound represented by Formula 26 were mixed at 3:7 as a host on the hole transport layer was used, and as a dopant, by doping Ir(ppy)₃ [tris(2-phenylpyridine)-iridium] at 95:5 weight, an emitting layer having a thickness of 30 nm was deposited on the hole transport layer. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

Comparative Example 13

An organic electroluminescent device was manufactured in the same manner as in Example 3, except that Comparative Compound 8 was used instead of the compound represented by Formula 25 of the present invention as a host material.

Comparative Example 14

An organic electroluminescent device was manufactured in the same manner as in Example 3, except that Comparative Compound 9 was used instead of the compound represented by Formula 25 of the present invention as a host material.

Comparative Example 15

Except for using Comparative Compound 10 instead of the compound represented by Formula 25 of the present invention as a host material, an organic electroluminescent device was manufactured in the same manner as in Example 3, except that Comparative Compound 12 was used instead of the compound represented by Formula 26 of the present invention.

Comparative Example 16

Except for using Comparative Compound 11 instead of the compound represented by Formula 25 of the present invention as a host material, an organic electroluminescent device was manufactured in the same manner as in Example 3, except that Comparative Compound 12 was used instead of the compound represented by Formula 26 of the present invention.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 5000 cd/m². In the following table 8, the manufacture of a device and the results of evaluation are shown.

TABLE 9 Current Brightness Efficiency 1^(st) host 2^(nd) host Voltage Density (cd/m²) (cd/A) T(95) comparative comparative 9-3 4.7 12.4 5000.0 40.2 125.1 example 13 compound A comparative comparative 4.9 12.3 5000.0 40.6 126.3 example 14 compound B comparative comparative comparative 4.9 11.7 5000.0 42.9 130.2 example 15 compound C compound E comparative comparative 5.0 12.1 5000.0 41.4 127.7 example 16 compound D example 71  7-20 9-1 4.3 9.6 5000.0 52.2 147.4 example 72 9-3 4.2 9.4 5000.0 53.2 146.0 example 73 9-6 4.3 9.7 5000.0 51.7 144.5 example 74 9-8 4.3 9.9 5000.0 50.7 143.1 example 75 8-1 9-1 4.2 9.8 5000.0 51.3 144.6 example 76 9-3 4.2 9.6 5000.0 52.3 143.2 example 77 9-6 4.3 9.8 5000.0 50.8 141.8 example 78 9-8 4.3 10.0 5000.0 49.8 140.4 example 79 8-5 9-1 4.3 10.1 5000.0 49.4 141.9 example 80 9-3 4.3 9.9 5000.0 50.3 140.5 example 81 9-6 4.4 10.2 5000.0 48.9 139.1 example 82 9-8 4.3 10.4 5000.0 47.9 137.7 example 83  8-22 9-1 4.4 10.5 5000.0 47.5 139.0 example 84 9-3 4.3 10.3 5000.0 48.4 137.6 example 85 9-6 4.4 10.6 5000.0 47.0 136.4 example 86 9-8 4.4 10.8 5000.0 46.1 135.0

As can be seen from the results of Table 8 above, when the material for an organic electroluminescent device of the present invention represented by Formula 25 and Formula 26 is mixed and used as a phosphorescent host (Examples 71 to 86), the driving voltage, efficiency, and lifespan were significantly improved compared to the devices mixed with the comparative compound (Comparative Examples 13 to 16). Comparing Comparative Compound A and Comparative Compound B with the compound of the present invention represented by Formula 25, the compound of the present invention represented by Formula 25 differs in that it has a structure in which a substituent group is further substituted with dibenzofuran or dibenzothiophene. This is expected to increase the stability against charge by bonding a substituent to dibenzofuran or dibenzothiophene.

Also, when comparing the comparative compound C and the compound of the present invention represented by Formula 25, in the case of the comparative compound C, both dibenzofuran or dibenzothiophene are bonded to triazine at position 1, but the compound of the present invention represented by Formula 25 differs in that the bonding positions of dibenzofuran or dibenzothiophene and triazine are different in positions 1 and 3. Comparing the comparative compound D and the compound of the present invention represented by Formula 25, in the compound of the present invention represented by compound 25, dibenzofuran or dibenzothiophene and triazine are bonded by a single bond, and in the case of Comparative Compound D, there is a difference in that a biphenyl group is bonded by a linker between dibenzofuran or dibenzothiophene and triazine. Bonding at the 3rd position compared to the 1st position of dibenzofuran or dibenzothiophene becomes partially linear in the structure of the compound, and this is expected to affect the charge mobility. Also, due to the linker, the energy level of the compound (e.g., HOMO level, LUMO level, T1 level, etc.) changes, and it seems that it affects the performance of the device.

Also, when comparing the comparative compound E and the compound of the present invention represented by Formula 26, there is a difference in that the positions of the substituents substituted on dibenzofuran or dibenzothiophene are different, and in the device results, Examples 71 to 86 using the compound of the present invention represented by Formula 26 showed remarkably excellent performance.

As can be seen from the device results, even with a similar structure, it is necessary to grasp the interrelationship of the compounds of the first host and the second host, depending on the type of substituent of the compound, the bonding position of the substituent, the presence or absence of a linker, etc., intermolecular interactions (e.g., hole mobility, electron mobility, charge balance, etc.) vary depending on the physical properties of the compound[e.g., energy level and deposition conditions (e.g. Td, etc.)] and the morphology of the compound, it seems that this result is derived by acting as a major factor in improving the device performance during device deposition.

In conclusion, when the compounds of the present invention are applied to a host (Examples 71 to 86), remarkably excellent effects in device performance can be confirmed, and it is judged that the synergistic effect between the compounds of the present invention capable of appropriate interaction between the first host and the second host is maximized.

Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the embodiment disclosed in the present invention is intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention.

INDUSTRIAL AVAILABILITY

The organic electric element and device according to the present invention have excellent characteristics of high luminance, high light emission and long life, and thus they has industrial applicability. 

What is claimed is:
 1. An organic electric element comprising a first electrode, a second electrode, and at least an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, and the emitting layer comprises a first host material represented by Formula 25 and a second host material represented by Formula 26:

wherein: 1) Ar²¹, Ar²², Ar²³ and Ar²⁴ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si, P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; 2) R³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; nitro; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si or P; a fused ring of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group, wherein in case a1, a2, a3, a4, b1, b2, b3 and/or b4 are 2 or more, a plurality of R³¹ or a plurality of R³² or a plurality of R³³ or a plurality of R³⁴ or a plurality of R³⁵ or a plurality of R³⁶ or a plurality of R³⁷ or a plurality of R³⁸, the plural groups being the same to or different from each other, may be bonded to each other to form an aromatic or a heteroaromatic ring, 3) a1, a2, a3, a4, b2 and b3 are each independently an integer of 0 to 3, b1 and b4 are each independently an integer of 0 to 4, 4) X²¹ and X²² are each independently O or S, and 5) B is a substituent represented by Formula 27:

wherein R³⁹ and R⁴⁰ are the same as the definition of R³¹, Ar²⁵ is the same as the definition of Ar²¹, X²³ is O or S, b5 and b6 are each independently an integer of 0 to 3, and

means the bonding position, wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group or aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane; siloxane; boron; germanium; cyano; nitro; a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxy group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ring formed by the combination thereof.
 2. The organic electric element of claim 1, wherein Formula 25 is represented by one of Formulas 25-1 to 25-4:

wherein R³¹, R³², R³³, R³⁴, a1, a2, a3, a4, Ar²¹, Ar²², Ar²³, X²¹ and X²² are defined the same as defined in claim
 1. 3. The organic electric element of claim 1, wherein Ar²¹, Ar²² and Ar²³ are each represented by one of Formulas Ar-1 to Ar-12:

wherein: 1) Z⁶¹, Z⁶², Z⁶³, Z⁶⁴ and Z⁶⁵ are each independently CR⁴⁶ or N, with the proviso that at least one of Z⁶¹, Z⁶², Z⁶³, Z⁶⁴ and Z⁶⁵ is N, 2) X²⁴ is O, S, CR⁴⁹R⁵⁰ or NR⁵¹, 3) R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁶ are defined the same as the definition of R³¹ in claim 1, 4) R⁴⁹, R⁵⁰ and R⁵¹ are each independently selected from the group consisting of hydrogen; deuterium; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₅₀ alkoxy group; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si, P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and R⁴⁹ and R⁵⁰ may be bonded to each other to form a spiro ring, 5) c1 is an integer of 0 to 5, c2, c5, c6 and c7 are each independently an integer of 0 to 4, c3 is an integer of 0 to 7, c4 is an integer of 0 to 3, 6)

M means the bonding position.
 4. The organic electric element of claim 1, wherein the compound represented by Formula 25 comprises any one of the following Compounds 7-10 to 7-20 and Compounds 8-1 to 8-38:


5. The organic electric element of claim 1, wherein B in Formula 26 is represented by one of Formulas 27-1 to 27-4:

wherein: 1) R³⁹, R⁴⁰, X²³, Ar²⁵, b5 and b6 are defined the same as in claim 1, 2)

means the bonding position.
 6. The organic electric element of claim 1, wherein B in Formula 26 is represented by one of Formulas 27-5 to 27-12:

wherein: 1) R³⁹, R⁴⁰, X²³, Ar²⁵, b5 and b6 are each defined the same as in claim 1, 2)

N means the bonding position.
 7. The organic electric element of claim 1, wherein the compound represented by Formula 26 is represented by one of Compounds 9-1 to 9-36:


8. The organic electric element of claim 1, further comprising a light efficiency-enhancing layer formed on either or both sides of the first electrode and the second electrode, the side being located opposite to the organic material layer and not facing the organic material layer.
 9. The organic electric element of claim 1, wherein the organic material layer comprises 2 or more stacks of layers including a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the first electrode.
 10. The organic electric element of claim 9, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks of layers.
 11. An electronic device comprising: a display device including the organic electric element of claim 1; and a control unit for driving the display device.
 12. An electronic device of claim 11, wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and an element for monochromic or white illumination. 